Recent advances in the synthesis of unnatural α-amino acids-an updated version

Current Organic Chemistry

Volumn 15, Issue 22, 2011, Pages 3750-3799

  Perdih, A ^a   Dolenc, M Sollner ^b  

^a NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^b UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Amino acid derivatives; Peptidomimetics; Synthesis; Unnatural amino acids

Indexed keywords

BIOCHEMISTRY; MOLECULES; ORGANOMETALLICS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ACTIVE PEPTIDES; AMINO ACID DERIVATIVES; AMINO-ACIDS; DE NOVO DESIGN; METABOLIC STABILITY; PEPTIDOMIMETICS; RELATED COMPOUNDS; SYNTHETIC METHODOLOGY; SYNTHETIC METHODS; UNNATURAL Α-AMINO ACID;

AMINO ACIDS;

EID: 80055076411     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211797884566     Document Type: Review

References (168)

1. Burger's Medicinal Chemistry and Drug Discovery, Volume 1, Drug Discovery, 6th Ed. John Wiley & Sons: New York, 2005.
2. Bonner, G.G.; Davis, P.; Stropova, C.; Ferguson, R.; Yamamura, H.I.; Porreca, F.; Hruby, V.J. Opioid Peptides: SimultaneousδAgonism andμAntagonism in Somatostatin Analogues. Peptides, 1997, 18, 93-100.
3. Marshall, S.A.; Lazar, G.A.; Chirino, A.; Desjarlais, J.R. Rational design and engineering of therapeutic proteins. Drug Discov. Today, 2003, 8, 212-221
4. Szymkowski, D.E. Rational optimization of proteins as drugs: a new era of 'medicinal biology. Drug Discov. Today, 2004, 9, 381-383.
5. Adessi, C.; Soto, C. Converting a Peptide into a Drug: Strategies to Improve Stability and Bioavailability. Curr. Med. Chem., 2002, 9, 963-978.
6. Gante, J. Peptidomimetics-Tailored Enzyme Inhibitors. Angew. Chem. Int. Ed. Engl., 1994, 33, 1699-1720.
7. Marshall, G.R. A hierarchical approach to peptidomimetic design. Tetrahedron, 1993, 49, 3547-3558.
8. Wang, L.; Schultz, P.G. Expanding the genetic code. Chem. Commun., 2002, 1-11.
9. Maruoka, K.; Ooi, T. Enantioselective Amino Acid Synthesis by Chiral Phase-Transfer Catalysis. Chem. Rev., 2003, 103, 3013-3028.
10. Risseeuw, M.D.P.; Overhand, M.; Fleet, G.W.J.; Simone, M.I. A compendium of sugar amino acids (SAA): scaffolds, peptide- and glyco-mimetics. Tetrahedron Asymmetry, 2007, 18, 2001-2010.
11. Estévez, R.J.; Smith M.D.; Lane, A.L.; Crook, S.; Watkin, D.J.; Bestra, G.S.; Brennan, P.J.; Nash, R.J.; Fleet, G.W.J. Mimics of L-rhamnose: Anomeric spirohydantoins and diketopiperazines-approaches to novel N-linked glycopeptides of rhamnofuranose. Tetrahedron Asymmetry, 1996, 7, 387-390.
12. Soengas, R.G.; Estévez, J.C.; Estévez, R.J. Total synthesis of 3, 4-dihydroxyprolines, D-threo-L -norvaline and (2S,3R,4R)-2-amino-3,4-dihydroxytetrahydrofuran-2-carboxylic acid methyl ester. Tetrahedron Asymmetry, 2003, 14, 3955-3963.
13. Soengas, R.G.; Begoña Pampín, M.; Estévez, J.C.; Ramon, J. Estévez, R.J. Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 2: Synthesis of (1S,2R,3S,4S,5R)-3,4,5-trihydroxy-2-aminocyclopentanecarboxylic acid. Tetrahedron Asymmetry, 2005, 16, 205-211.
14. Hendrickson, T.L.; Crécy-Lagard, V.; Schimmel, P. Incorporation of nonnatural amino acids into proteins. Annual Review of Biochemistry, 2004, 73,147-176.
15. Lu, Y. Design and engineering of metalloproteins containing unnatural amino acids or non-native metal-containing cofactors. Curr. Opin. Chem. Biol., 2005, 9, 118-126.
16. Beene, D.L.; Dougherty, D.A.; Lester, H.A. Unnatural amino acid mutagenesis in mapping ion channel function. Curr. Opin. Neurobiol., 2003, 13, 267.
17. Hyun, M.H.; Han, S.C.; Lipshutz, B.H.; Shin, Y.-J.; Welch, C.J. New chiral crown ether stationary phase for the liquid chromatographic resolution of alpha-amino acid enantiomers. J. of Chromatogr. A, 2001, 910, 359-365.
18. Jin, J.S.; Stalcup, A.M.; Hyun, M.H. Impact of triethylamine as a mobile phase additive on the resolution of racemic amino acids on an (+)-18-crown-6- tetracarboxylic acid-derived chiral stationary phase. J. of Chromatogr. A, 2001, 933, 83-90.
19. Péter, A.; Árki, A.; Vékes, E.; Tourwé, D.; Lázár, L.; Fülöp, F.; Armstrong, D.W. Direct and indirect high-performance liquid chromatographic enantioseparation of α-amino acids. J. of Chromatogr. A, 2004, 1031, 171-178.
20. Trabocchi, A.; Scarpi, D.; Guarna, A. Structural diversity of bicyclic amino acids. Amino Acids, 2008, 34, 1-24.
21. Soloshonok, V.A.; Sorochinsky, A.E.; Practical Methods for the Synthesis of Symmetrically alpha,alpha-Disubstituted alpha-Amino Acids. Synthesis, 2010, 14, 2319-2344.
22. Perdih, A.; Dolenc, M.S. Recent advances in the synthesis of unnatural alpha-amino acids. Curr Org. Chem. 2007, 11, 801-832.
23. Gallos, J.K.; Sarli, V.C.; Varvogli, A.C.; Papadoyanni, C.Z.; Papaspyrou, S.D.; Argyropoulos, N.G. The hetero-Diels-Alder addition of ethyl 2-nitrosoacrylate to electron-rich alkenes as a route to unnatural alpha-amino acids. Tetrahedron Lett., 2003, 44, 3905-3909.
24. Gallos, J.K.; Sarli, V.C.; Massen, Z.S.; Varvogli, A.C.; Papadoyanni, C.Z.; Papaspyrou, S.D.; Argyropoulos, N.G. A new strategy for the stereoselective synthesis of unnatural α-amino acids. Tetrahedron, 2005, 61, 565-574.
25. Dygos, J.H.; Yonan, E.E.; Scros, M.G.; Goodmonson, O.J.; Getman, D.P.; Periana, R.A.; Beck, G.R. A convenient asymmetric-synthesis of the unnatural amino-acid 2,6-dimethyl-L-Tyrosine. Synthesis, 1992, 741-743.
26. Balducci, D.; Contaldi, S.; Lazzari, I.; Porzi, G. A highly efficient stereocontrolled synthesis of (S)-2 ',6 '-dimethyltyrosine [(S)-DMT]. Tetrahedron Asymmetry, 2009, 20, 1398-1401.
27. Tang, X.; Soloshonok, V. A.; Hruby, V. J. Convenient, asymmetric synthesis of enantiomerically pure 2_,6α-dimethyltyrosine (DMT) via alkylation of chiral equivalent of nucleophilic glycine. Tetrahedron: Asymmetry, 2000, 11, 2917-2925.
28. Soloshonok, V. A.; Tang, X.; Hruby, V. J. Large-scale asymmetric synthesis of novel sterically constrained 2',6'-dimethyl- and α,2',6'-trimethyltyrosine and -phenylalanine derivatives via alkylation of chiral equivalents of nucleophilic glycine and alanine. Tetrahedron, 2001, 57, 6375-6382.
29. Qiu, W.; Soloshonok, V. A.; Cai, C.; Tang, X.; Hruby, V. J. Convenient, Large-Scale Asymmetric Synthesis of Enantiomerically Pure trans-Cinnamylglycine and -α- Alanine. Tetrahedron, 2000, 56, 2577-2582.
30. Wasserman, H.H.; Long, Y.O.; Parr, J. α,β-Diketo nitriles as dielectrophiles. Formation of heterocyclic derivatives of amino acids. Tetrahedron Lett., 2003, 44, 361-363.
31. Boto, A.; Hernandez, R.; Montoya, A.; Suarez, E. One-pot synthesis of aryl glycines and other unnatural amino acids from serine derivatives. Tetrahedron Lett., 2002, 43, 8269-8272.
32. Boto, A.; Gallardo, J.A.; Hernandez, D.; Hernandez, R.; Synthesis of Unnatural Amino Acids from Serine Derivatives by β -Fragmentation of Primary Alkoxyl Radicals. J. Org. Chem., 2007, 72, 7260-7269.
33. Yu, G.; Mason, H.J.; Galdi, K.; Wu, X.; Cornelius, L.; Zhao, N.; Witkus, M.; Ewing, W.R.; Macor, J.E. Mono-chlorination of electron-rich arylalkyl- and heteroarylalkyl-amines and amino acids using sulfuryl chloride. Synthesis, 2003, 403-407.
34. Ray, D.; Nyong, A.M.; Natarajana, A. Synthesis of unnatural amino acid derivatives via palladium-catalyzed 1,4-addition of boronic acids. Tetrahedron Lett., 2010, 51, 2655-2656.
35. Huang, T.S.; Li, C.J. Novel synthesis of alpha-amino acids via catalysis in air and water. Org. Lett., 2001, 3, 2037-2039.
36. Cheng, H.; Luzy, J.-P.; Garbay, C. A new efficient enantioselective synthesis of malonylphenylalanyl and malonylmethylphenylalanyl derivatives suitable for solid phase peptide synthesis. Tetrahedron Lett., 2005, 46, 3319-3322.
37. Shieh, W.-C.; Xue, S.; Reel, N.; Wu, R.; Fitt, R.; Repič, O. An enantioselective synthesis of (R)-4-piperidinylglycine. Tetrahedron Asymmetry, 2001, 12, 2421-2425.
38. Padrón, J.M.; Kokotos, G.; Martín, T.; Markidis, T.; Gibbons, W.A.; Martín, V.A. Enantiospecific synthesis of alpha-amino acid semialdehydes: a key step for the synthesis of unnatural unsaturated and saturated alpha-amino acids. Tetrahedron Asymmetry, 1998, 9, 3381-3394.
39. Markidis, T.; Kokotos, G. Synthesis of enantiopure omega-functionalized C15 alpha-amino carboxylates. J. Org. Chem., 2002, 67, 1685-1688.
40. Jirgensons, A.; Marinozzi, M.; Pellicciari, R. Conformationally constrained amino acids: enantiodivergent synthesis of all four stereoisomers of 2-(tetrahydrofuran-2-yl)glycine. Tetrahedron, 2005, 61, 373-377.
41. Dondoni, A.; Massi, A.; Minghini, E.; Bertolasi, V. Multicomponent Hantzsch cyclocondensation as a route to highly functionalized 2- and 4-dihydropyridylalanines, 2- and 4-pyridylalanines, and their N-oxides: preparation via a polymer-assisted solution-phase approach. Tetrahedron, 2004, 60, 2311-2326.
42. Koskinen, A.M.P.; Hassilla, H.; Myllymäki, V.T.; Rissanen, K. Stereocontrolled conversion of L-Serine into a series of valuable unnatural α-aminoacids. Tetrahedron Lett., 1995, 36, 5619-5622.
43. Park, C.; Choi, H.; Son, Y.-C.; Lee, C.S.; Choy, N.; Koh, J.S.; Lee, T.G.; Kwon, Y.D.; Kim, S.C.; Yoon, H. β-methanesulfonyl-L-Valine as a novel, unnatural amino acid surrogate for P-2 in the design of HIV protease inhibitors. Bioorg. Med. Chem., 1996, 6, 585-588.
44. Loving, G.; Imperiali, B. A versatile amino acid analogue of the solvatochromic fluorophore 4-N,N-dimethylamino-1,8-naphthalimide: A powerful tool for the study of dynamic protein interactions. J. Am. Chem. Soc., 2008, 130, 13630-13638.
45. Guzow, K.; Kornowska, K.; Wiczk, W. Synthesis and photophysical properties of a new amino acid possessing a BODIPY moiety. Tetrahedron Lett., 2009, 50, 2908-2910.
46. Costa, S.P.G.; Oliveira, E.; Lodeiro, C.; Manuela, M.; Raposo, M. Heteroaromatic alanine derivatives bearing (oligo)thiophene units: synthesis and photophysical properties. Tetrahedron Lett., 2009, 49, 5258-5261.
47. Martin, N.I.; Woodward, J.J.; Winter, M.B.; Beeson, W.T.; Marletta, M.A. Design and synthesis of C5 methylated L-arginine analogues as active site probes for nitric oxide synthase. J. Am. Chem. Soc., 2007, 129, 12563-12570.
48. Swift, M.D.; Sutherland, A. Studies on the aza-Claisen rearrangement of 4,5 dihydroxylated allylic trichloroacetimidates: the stereoselective synthesis of (2R,3S) and (2S,3S)-2-amino-3,4-dihydroxybutyric acids. Tetrahedron, 2008, 64, 9521-9527.
49. Gorohovsky, S.; Meir, S.; Shkoulev, V.; Byk, G.; Gellerman, G. A facile two-step synthesis of novel ring-a double substituted tryptophan building blocks for combinatorial chemistry. Synlett, 2003, 1411-1414.
50. Carlier, P.; Lam, P.C.H.; Wong, D.M. Catalytic asymmetric synthesis of protected tryptophan regioisomers J. Org. Chem., 2002, 67, 6256-6259.
51. Blaser, G.; Sanderson, J.M.; Batsanov, A.S.; Howard, J.A.K. The facile synthesis of a series of tryptophan derivatives. Tetrahedron Lett., 2008, 49, 2795-2798.
52. Middleton, R.J.; Mellor, S.J.; Chhabra, S.R.; Bycroft, B.W.; Chan, W.C. Expedient synthesis of a novel class of pseudoaromatic amino acids: tetrahydroindazol- 3-yl- and tetrahydrobenzisoxazol-3-ylalanine derivatives. Tetrahedron Lett., 2004, 45, 1237-1242.
53. Hanessian, S.; Yang, R.-Y. The asymmetric synthesis of allylglycine and other unnatural alpha-amino acids via zinc-mediated allylation of oximes in aqueous media. Tetrahedron Lett., 1996, 37, 5273-5276.
54. Tanaka, K.; Ahn, M.; Watanabe, Y.; Fuji, K. Asymmetric synthesis of uncommon α-amino acids by diastereoselective alkylations of a chiral glycine equivalent. Tetrahedron Asymmetry, 1996, 7, 1771-1782.
55. Wang, W.; Wang, J.; Li, H. Catalysis of highly stereoselective Mannich-type reactions of ketones with β-imino esters by a pyrrolidine-sulfonamide. Synthesis of unnatural α-amino acids. Tetrahedron Lett., 2004, 45, 7243-7246.
56. Capone, S.; Guaragna, A.; Palumbo, G.; Pedatella, S. Efficient synthesis of orthogonally protected anti-2,3-diamino acids. Tetrahedron, 2005, 61, 6575-6579.
57. Kim, H.J.; Lee, S.; Park, Y.S. Alkylation of N'-[(S)-1'-phenylethyl]-N-(diphenylmethylene)glycinamide using a phase transfer catalyst (PTC) for practical asymmetric syntheses of α -amino acid derivatives. Synlett, 2001, 5, 613-616.
58. Ballini, R.; Balsamini, C.; Bartoccini, F.; Gianotti, M.; Martinelli, C.; Savoretti, N. Improved synthesis of γ-nitro-α-amino ester and acid derivatives. Synthesis, 2005, 296-299.
59. Young, D.D.; Torres-Kolbus, J.; Deiters, A. Microwave-assisted synthesis of unnatural amino acids. Bioorg. Med. Chem. Lett., 2008, 18, 5478-5480.
60. Oba, M.; Tanaka, M.; Takano, Y.; Suemune. H. Concise synthetic strategy toward cyclic α, α -disubstituted α -amino acids bearing a δ-nitrogen atom: Chiral 1-substituted 4-aminopiperidine-4-carboxylic acids. Tetrahedron, 2005, 61, 593-598.
61. Ellis, T.K.; Martin, C.H.; Tsai, G.H.; Ueki, H.; Soloshonok, V.A. Efficient synthesis of sterically constrained symmetrically α,α-disubstituted α-amino acids under operationally convenient conditions. J. Org. Chem., 2003, 68, 6208-6214.
62. Ueki, H.; Ellis, T.K.; Collin, M.H.; Soloshonok, V.A. Efficient Large-Scale Synthesis of Picolinic Acid-Derived Nickel(II) Complexes of Glycine. Eur. J. Org. Chem., 2003, 1954-1957.
63. Soloshonok, V. A.; Tang, X.; Hruby, V. J.; Meervelt, L.V. Asymmetric Synthesis of α,β-Dialkyl- α -phenylalanines via Direct Alkylation of a Chiral Alanine Derivative with Racemic α -Alkylbenzyl Bromides. A Case of High Enantiomer Differentiation at Room Temperature. Org. Lett., 2001, 3, 341-343.
64. Belokon, Y.N.; Bespalova, N.B.; Churkina, T.D.; Cisarova, I.; Ezernitskaya, M.G.; Harutyunyan, S.R.; Hrdina, R.; Kagan, H.B.; Kocovsky, P.; Kochetkov, K.A.; Larionov, O.V.; Lyssenko, K.A.; North, M.; Polasek, M.; Peregudov, A.S.; Prisyazhnyuk, V.V.; Vyskocil, S. Synthesis of α -amino acids via asymmetric phase transfer-catalyzed alkylation of achiral nickel(II) complexes of glycine-derived Schiff bases. J. Am. Chem. Soc., 2003; 125, 12860-12871.
65. Miyabe, H.; Asada, R.; Takemoto, Y. Synthesis of α, α -disubstituted amino acids based on tandem reaction of dehydroamino acid derivatives. Tetrahedron, 2005, 61, 385-393.
66. Chowdari, N.S.; Suri, J.T.; Barbas, C.F. III Asymmetric synthesis of quaternary α-and β -amino acids and β -lactams via proline-catalyzed Mannich reactions with branched aldehyde donors. Org. Lett., 2004, 6, 2507-2510.
67. Davis, F.A.; Zhang, Y.; Rao, A.; Zhang, Z. Aziridine mediated asymmetric synthesis of α -benzylserine and α -n-butylserine. Tetrahedron, 2001, 57, 6345-6352.
68. Tsubogo, T.; Kano, Y.; Ikemoto, K.; Yamashita, Y.; Kobayashi, S. Synthesis of optically active, unnatural α -substituted glutamic acid derivatives by a chiral calcium-catalyzed 1,4-addition reaction. Tetrahedron Asymmetry, 2010, 21, 1221-1225.
69. Warmuth, R.; Munsch, T.E.; Stalker, R.A.; Li, B.; Beatty, A. Enantioselective synthesis of benzocyclic α, α -dialkyl-amino acids: new insight into the solvent dependent stereoselectivity of the TMSCN addition to phenylglycinol derived imines. Tetrahedron, 2001, 57, 6383-6397.
70. Maity, P.; Zabel, M.; König, B. Tetrahydrofuran C α-tetrasubstituted amino acids: Two consecutive β -turns in a crystalline linear tripeptide J. Org. Chem., 2007, 72, 8046-8053.
71. Grauer, A.A.; Köning, B. Synthesis of new C- α -tetrasubstituted alpha-amino acids. Beilstein J. Org. Chem., 2009, 5, No 5.
72. van Esseveldt, B.C.J.; van Delft, F.L.; Smits, J.M.M.; de Gelder, R.; Rutjes, F.P.J.T. Pd-catalysed synthesis of 5-substituted proline derivatives from acetylene-containing amino acids. Synlett, 2003, 15, 2354-2358.
73. van Esseveldt, B.C.J.; van Delft, F.L.; de Gelder, R.; Rutjes, F.P.J.T. Palladium-catalyzed synthesis of novel optically active tryptophan analogues. Org. Lett., 2003, 5, 1717-1720.
74. Cheng, W.-C.; Liu, Y.; Wong, M.; Olmstead, M.M.; Lam, K.S, Kurth, M.J. Stereoselective synthesis of unnatural spiroisoxazolinoproline-based amino acids and Derivatives. J. Org. Chem., 2002, 67, 5673-5677.
75. Tiwari, S.K.; Schneider, A.; Koep, S.; Gais, H.-J. Asymmetric synthesis of 3-substituted unsaturated prolines from chiral sulfoximine substituted allyl titanium(IV) complexes. Tetrahedron Lett., 2004, 45, 8343-8346.
76. da Costa, J.F.; Caamaño, O.; Fernández, F.; García-Mera, X.; Midón, P.; Rodríguez-Borges, J.E. Synthesis of methyl (±)-3,5- bis(substitutedmethyl)pyrrolidine-2-carboxylates: a convenient approach to proline-mimetics. Tetrahedron, 2010, 66, 6797-6805.
77. Mitsunaga, S.; Ohbayashi, T.; Sugiyama, S.; Saitou, T.; Tadokoro, M.; Satoh, T. Asymmetric synthesis of cyclic α -amino acid derivatives by the intramolecular reaction of magnesium carbenoid with an N-magnesio arylamine.Tetrahedron Asymmetry, 2009, 20, 1697-1708.
78. Soloshonok, V.A.; Cai, C.; Hruby, V.J.; Meervelt, L.V.; Mischenko, N. Stereochemically defined C-substituted glutamic acids and their derivatives. 1. An efficient asymmetric synthesis of (2S,3S)-3-methyl- and -3- trifluoromethylpyroglutamic acids. Tetrahedron, 1999, 55, 12031-12044.
79. Soloshonok, V.A.; Cai, C.; Hruby, V.J.; Meervelt, L.V. Asymmetric synthesis of novel highly sterically constrained (2S,3S)-3-methyl-3-trifluoromethyland (2S,3S,4R)-3-trifluoromethyl-4-methylpyroglutamic acids. Tetrahedron, 1999, 55, 12045-12058.
80. Soloshonok, V.A.; Cai, C.; Hruby, V.J. Asymmetric Michael addition reactions of chiral Ni(II)-complex of glycine with (N-trans-enoyl)oxazolidines: improved reactivity and stereochemical outcome. Tetrahedron: Asymmetry, 1999, 10, 4265-4269.
81. Soloshonok, V.A.; Cai, C.; Hruby, V.J. Toward design of a practical methodology for stereocontrolled synthesis of χ-constrained pyroglutamic acids and related compounds. Virtually complete control of simple diastereoselectivity in the Michael addition reactions of glycine Ni(II) complexes with N- (enoyl)oxazolidinones. Tetrahedron Lett., 2000, 41, 135-139.
82. Soloshonok, V.A.; Cai, C.; Hruby, V.J. (S)- or (R)-3-(E-Enoyl)-4-phenyl- 1,3- oxazolidin-2-ones: Ideal Michael Acceptors To Afford a Virtually Complete Control of Simple and Face Diastereoselectivity in Addition Reactions with Glycine Derivatives. Org. Lett., 2000, 2, 747-750.
83. Soloshonok, V.A.; Cai, C.; Hruby, V.J. A Practical Asymmetric Synthesis of Enantiomerically Pure 3-Substituted Pyroglutamic Acids and Related Compounds. Angew. Chem. Int. Ed., 2000, 39, 2172-2175.
84. Soloshonok, V.A.; Cai, C.; Hruby, V.J.; Meervelt, L.V.; Yamazaki, T. Rational Design of Highly Diastereoselective, Organic Base-Catalyzed, Room. Temperature Michael Addition Reactions. J. Org. Chem., 2000, 65, 6688-6696.
85. Soloshonok, V.A.; Cai, C.; Hruby, V.J. A unique case of face diastereoselectivity in the Michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3-oxazolidin-2-ones. Tetrahedron Lett., 2000, 41, 9645-9649.
86. Cai, C.; Soloshonok, V.A.; Hruby, V.J. Michael addition reactions between chiral Ni (II) donor-acceptor attractive interaction-controlled face diastereoselectivity. J. Org. Chem., 2001, 66, 1339-1350.
87. Soloshonok, V. A.; Ueki, H.; Tiwari, R.; Cai, C.; Hruby, V. J. Virtually Complete Control of Simple and Face Diastereoselectivity in the Michael Addition Reactions between Achiral Equivalents of a Nucleophilic Glycine and (S)- or (R)-3-(E-Enoyl)-4-phenyl-1,3-oxazolidin-2-ones: Practical Method for Preparation of β-Substituted Pyroglutamic Acids and Prolines. J. Org. Chem., 2004, 69, 4984-4990.
88. Cai, C.; Yamada, T.; Tiwari, R.; Hruby, V. J.; Soloshonok, V. A. Application of (S)- and (R)-methyl pyroglutamates as inexpensive, yet highly efficient chiral auxiliaries in the asymmetric Michael addition reactions. Tetrahedron Lett. 2004, 45, 6855-6858.
89. Soloshonok, V. A.; Cai, C.; Yamada, T.; Ueki, H.; Ohfune, Y.; Hruby, V. J. Michael Addition Reactions between Chiral Equivalents of a Nucleophilic Glycine and (S)- or (R)-3-[(E)-Enoyl]-4-phenyl-1,3-oxazolidin-2-ones as a General Method for Efficient Preparation of β-Substituted Pyroglutamic Acids. Case of Topographically Controlled Stereoselectivity. J. Am. Chem. Soc. 2005, 127, 15296-15303.
90. Lautens, M.; Tayama, E.; Nguyen, D. Direct vinylogous Mannich-type reactions via ring opening and rearrangement of vinyloxiranes. Org. Lett., 2004, 6, 345-347.
91. Södergren, M.J.; Andersson, P.G. Chiral, bicyclic proline derivatives and their application as ligands for copper in the catalytic asymmetric allylic oxidation of olefins. Tetrahedron Lett., 1996, 37, 7577-7580.
92. Depew, K.M.; Kamenecka T.M.; Danishefsky, S.J. Enantioselective synthesis of protected forms of (3R,5R)-5-hydroxypiperazic acid useful for synthesis. Tetrahedron Lett., 2000, 41, 289-292.
93. Kennedy, J.P.; Lindsley, C.W. Progress towards the synthesis of piperazimycin A: Synthesis of the non-proteogenic amino acids and elaboration into dipeptides. Tetrahedron Lett., 2010, 51, 2493-2496.
94. Aurelio, L.; Brownlee, R.T.C.; Hughes, A.B. Synthetic preparation of Nmethyl-alpha amino acids. Chem. Rev., 2004, 104, 5823-5846.
95. Biron, E.; Kessler, H. Convenient Synthesis of N-Methylamino Acids Compatible with Fmoc Solid-Phase Peptide Synthesis. J. Org. Chem., 2005, 70, 5183-5189.
96. White, K.N., Konopelski, J.P. Facile synthesis of highly functionalized Nmethyl amino acid esters without side-chain protection. Org. Lett., 2005, 7, 4111-4112.
97. Freidinger, R.M.; Hinkle, J.S.; Perlow, D.S.; Arison, B.H. Synthesis of 9- fluorenylmethyloxycarbonyl-protected n-alkyl amino-acids by reduction of oxazolidinones. J. Org. Chem., 1983, 48, 77-81.
98. Aurelio, L.; Brownlee, R.T.C.; Hughes, A.B.; Sleebs, B.E. The facile production of N-methyl amino acids via oxazolidinones. Aust. J. Chem., 2000, 53, 425-433.
99. Zhang, S.; Govender, T.; Norström, T.; Arvidsson, P.I. An improved synthesis of Fmoc-N-methyl-alpha-amino acids. J. Org. Chem., 2005, 70, 6918-6920.
100. Izzo, I.; Avallone, E.; Della Corte, L.; Maulucci, N.; De Riccardis. Asymmetric synthesis of N,O-diprotected (2S,3S)-N-methy-δ-hydroxyisoleucine, noncoded amino acid of halipeptin A. Tetrahedron Asymmetry, 2004, 15, 1181-1186.
101. Malkov, A.V.; Vrankova, K.; Cerny, M.; Ko-ovsky P. On the Selective NMethylation of BOC-Protected Amino Acids. J. Org. Chem., 2007, 74, 8425-8427.
102. Muramatsu, H.; Mihara, H.; Kakutani, R.; Yasuda, M.; Ueda, M.; Kurihara, T.; Esaki, N. Enzymatic synthesis of N-methyl-L-phenylalanine by a novel enzyme, N-methyl-L-amino acid dehydrogenase, from Pseudomonas putida. Tetrahedron Asymmetry, 2004, 15, 2841-2843.
103. Tandom, V.K.; Yadav, D.B.; Singh, R.V.; Chaturvedi, A.K.; Shukla, P.S. Synthesis and biological evaluation of novel (L)-alpha-amino acid methyl ester, heteroalkyl, and aryl substituted 1,4-naphthoquinone derivatives as antifungal and antibacterial agents. Bioorg. Med. Chem Lett., 2005, 15, 5324-5328.
104. Jiang, Y.; Tan, B.; Chen, Z.Z.; Liu, T.; Zhong, R.G.; Li, Y.M.; Stewart, D.J.; Zhao Y.F.; Jiang, H.L. Phosphoryl group differentiating α -amino acids from β- and γ-amino acids in prebiotic peptide formation. Int. J. Quantum Chem., 2003, 94, 232-241.
105. Wu, L.Y.; Berkman, C.E. Synthesis of N-phosphoryl amino acids using bis(9-fluorenylmethyl)phosphite. Tetrahedron Lett., 2005, 46, 5301-5303.
106. O'Donnell, M.J.; Zhou, C.; Scott, W.L. Solid-phase unnatural peptide synthesis (UPS). J. Am. Chem. Soc., 1996, 118, 6070-6071.
107. Scott, W.L.; Zhou, C.; Fang, Z.; O'Donnell, M.J. The solid phase synthesis of alpha,alpha-disubstituted unnatural amino acids and peptides (di-UPS). Tetrahedron. Lett., 1997, 38, 3695-3698.
108. O'Donnell, M.J.; Lugar, C.W.; Pottorf, R.S.; Zhou, C. Solid-phase synthesis of unnatural amino acids using unactivated alkyl halides. Tetrahedron Lett., 1997, 38, 7163-7166.
109. Domínguez, E.; O'Donnell, M.J.; Scott, W.L. Solid-phase synthesis of substituted glutamic acid derivatives via Michael addition reactions. Tetrahedron Lett., 1998, 39, 2167-2170.
110. O'Donnell, M.J.; Delgado, F.; Drew, M.D.; Pottorf, M.D.; Zhou, C.; Scott, W.L. Solid-phase synthesis of unnatural α-amino acid derivatives using a resin-bound glycine cation equivalent. Tetrahedron Lett., 1999, 40, 5831-5835.
111. Scott, W.L.; Delgado, F.; Lobb, K.; Pottorf, M.D.; O'Donnell, M.J. Solidphase synthesis of amino amides and peptide amides with unnatural side chains. Tetrahedron Lett., 2001, 42, 2073-2076.
112. Scott W.L.; O'Donnell, M.J.; Delgado, F.; Alsina, J. A solid-phase synthetic route to unnatural amino acids with diverse side-chain substitutions. J. Org. Chem. 2002, 67, 2960-2969.
113. O'Donnell, M.J.; Alsina, J.; Scott, W.L. Solid-phase synthesis and utilization of side-chain reactive unnatural amino acids. Tetrahedron Lett., 2003, 44, 8403-8406.
114. Scott, W.L.; Zhou, Z.N.; Martynow, J.G.; O'Donnell, M.J. Solid-Phase Synthesis of Amino- and Carboxyl-Functionalized Unnatural α-Amino Acid Amides. Org. Lett., 2009, 11, 3558-3561.
115. Scott, W.L.; O'Donnell, M.J. Distributed Drug Discovery, Part 1: Linking Academia and Combinatorial Chemistry to Find Drug Leads for Developing World Diseases J. Comb. Chem., 2009, 11, 3-13.
116. Scott, W.L.; Alsina, J.; Audu, C.O.; Babaev, E.; Cook, L.; Dage, J. L.; Goodwin, L. A.; Martynow, J.G.; Matosiuk, D.; Royo, M.; Smith, J.G.; Strong, A.T.; Wickizer, K.; Woerly, E.M.; Zhou, Z.; O'Donnell, M.J. Distributed Drug Discovery, Part 2: Global Rehearsal of Alkylating Agents for the Synthesis of Resin-Bound Unnatural Amino Acids and Virtual D-3 Catalog Construction. J. Comb. Chem., 2009, 11, 14-33.
117. Scott, W.L.; Audu, C.O.; Dage, J.L.; Goodwin, L.A.; Martynow, J.G.; Platt, L.K; Smith, J.G.; Strong, A.T.; Wickizer, K.; Woerly, E.M.; O'Donnell, M.J. Distributed Drug Discovery, Part 3: Using D-3 Methodology to Synthesize Analogs of an Anti Melanoma Compound. J. Comb. Chem. 2009, 11, 34-43.
118. Staszewska, A.; Stefanowicz, P.; Szewczuk, Z. Direct solid-phase synthesis of quinoxaline-containing peptides. Tetrahedron Lett., 2005, 46, 5525-5528.
119. Paris, M.; Douat, C.; Heitz, A.; Gibbons, W.; Martinez, J.; Fehrentz J.-A. Post-synthesis modification of aspartyl or glutamyl residue side-chains on solid support. Tetrahedron Lett., 1999, 40, 5179-5182.
120. Patkar, K.A.; Highsmith, W.E.; Aldrich, J.V. Solid phase and solution synthesis of NvocLys(CO(CH2)(5)NH-NBD)OCH2CN, a trifunctional fluorescent lysine derivative. Amino Acids, 2009, 36, 203-207.
121. Kabalka, G.W.; Das, B.C.; Das, S. Synthesis of novel boron containing unnatural cyclic amino acids as potential therapeutic agents. Tetrahedron Lett., 2001, 42, 7145-7146.
122. Kabalka, G.W.; Wu, Z.Z.; Yao, M.-L.; Natarajan, N. The syntheses and in vivo biodistribution of novel boronated unnatural amino acids. Applied Radiation and Isotopes, 2003, 61, 1111-1115.
123. Kabalka, G.W.; Yao, M.-L. Synthesis of a potential boron neutron capture therapy agent: 1-aminocyclobutane-1-carboxylic acid bearing a butylboronic acid side chain. Synthesis, 2003, 2890-2893.
124. Kabalka, G.W.; Yao, M.-L. Synthesis of 1-amino-3- [(dihydroxyboryl)methyl]-cyclobutanecarboxylic acid as a potential therapy agent. J. Org. Chem., 2004, 69, 8280-8286.
125. Kabalka, G.W.; Yao, M.-L.; Navarane, A. Synthesis of a boronated amino acid as a potential neutron therapy agent: 1-amino-3- [(dihydroxyboryl)ethyl]-cyclobutanecarboxylic acid. Tetrahedron Lett., 2005, 46, 4915-4917.
126. Kabalka, G.W.; Wu, Z.Z.; Yao, M.L. Synthesis of a series of boronated unnatural cyclic amino acids as potential boron neutron capture therapy agents. Appl. Organomet. Chem., 2008, 22 516-522.
127. Greenfield, S.J.; Gilbertson, S.R. Preparation of diphenylphosphinoserine and synthesis of other phosphine containing amino acids using zinc/copper reagents. Synthesis, 2001, 10, 2337-2340.
128. Davis, F.A.; Lee, S.; Yan, H.; Titus, D.D. Asymmetric synthesis of quaternary α-amino phosphonates using sulfinimines. Org. Lett., 2001, 3, 1757-1760.
129. Lach, J.; Guo, C.Y.; Kindermann, M.K.; α-Phosphanyl Amino Acids: Synthesis, Structure and Reactivity of N-Aryl-alpha-phosphanylglycines. Eur. J. Org. Chem., 2010,1176-1186.
130. Birkofer, L.; Ritter, A. Neue Silicium-Organische Verbindungen-Silicoaminosauren und Silazan-Carbonsaureester. Angew. Chem., 1956, 68, 461-462.
131. Sieburth, S. McN.; Somers, J.J.; O'Hare, H.K. α-alkyl-α-aminosilanes. 1. Metalation and alkylation between silicon and nitrogen. Tetrahedron, 1996, 52, 5669-5682.
132. Liu, G.; Sieburth, S.M. Enantioselective alpha-silyl amino acid synthesis by reverse-aza-brook rearrangement. Org. Lett., 2003, 5, 4677-4679.
133. Falgner, S.; Schmidt, D.; Bertermann, R.; Buschka, C.; Tacke, R. Novel Synthesis and Crystal Structure Analysis of rac-β-(Trimethylsilyl)alanine. Organometallics, 2009, 28, 2927-2930.
134. Falgner, S.; Burschka, C.; Wagner, S.; Böhm, A.; Daiss J.O.; Tacke, R. Asymmetric Synthesis of the Nonproteinogenic Silicon-Containing alpha-Amino Acids (R)- and (S)-α-[(Trimethylsilyl)methyl]alanine. Organometallics, 2009, 28, 6059-6066.
135. Degani, V.; Heller, A. Direct electrical communication between chemically modified enzymes and metal-electrodes. 2. Methods for bonding electrontransfer relays to glucose-oxidase and d-amino-acid oxidase. J. Am. Chem. Soc., 1988, 110, 2615-2620.
136. Kira, M.; Matsubara, T.; Shinohara, H.; Sisido, M. Synthesis and redox property of polypeptides containing L-ferrocenylalanine. Chem. Lett., 1997, 89-90.
137. Brosch, O.; Weyhermüller, T.; Metzler-Nolte, N. A two-step palladiumcatalyzed coupling scheme for the synthesis of ferrocene-labeled amino acids. Eur. J. Inorg. Chem., 2000, 323-330.
138. Barišić, L.; Rapić, V.; Pritzkow, H.; Pavlovi-, G.; Nemet, I. Ferrocene compounds Part XXXIII. Synthesis and characterization of amino acids containing skeletal 1,1 '-ferrocenylene unit. J. Organomet. Chem., 2003, 682, 131-142.
139. Kuik, A.; Skoda-Földes, R.; Balogh, J.; Kollár, L. Synthesis of ferrocenoyl amino acid derivatives via homogeneous catalytic aminocarbonylation. J. Organomet. Chem., 2005, 690, 3237-3242.
140. Savage, D.; Malone, G.; Alley, S.R.; Gallagher, J.F.; Goel, A.; Kelly, P.N.; Bunz, H.M.; Kenny, P.T.M. The synthesis and structural characterization of N-ortho-ferrocenyl benzoyl amino acid esters. The X-ray crystal structure of N-{ortho-(ferrocenyl)benzoyl}-L-phenylalanine ethyl ester. J. Organomet. Chem., 2006, 691, 463-469.
141. Savage, D.; Neary, N.; Malone, G.; Alley, S.R.; Kenny, P.T.M. The synthesis and structural characterization of novel N-meta-ferrocenyl benzoyl amino acid esters. Inorg. Chem. Commun. 2005, 8, 429-432.
142. Tippmann, E.M.; Schultz, P.G. A genetically encoded metallocene containing amino acid. Tetrahedron, 2007, 63, 6182-6184.
143. Gellett, A.M.; Huber, P.W.; Higgins, P.J. Synthesis of the unnatural amino acid N-alpha-N-epsilon-(ferrocene-1-acetyl)-L-lysine: A novel organometallic nuclease. J. Organomet. Chem., 2008, 693, 2959-2962.
144. Ardá, A.; Jiménez, C.; Rodríguez, J. A study of polychlorinated leucine derivatives: synthesis of (2S,4S)-5,5-dichloroleucine. Tetrahedron Lett., 2004, 45, 3241-3243.
145. Bravo, P.; Capelli, S.; Meille, S.V.; Seresini, P.; Volonterio, A.; Zanda, M. Enantiomerically pure α-fluoroalkyl-α-amino acids: Synthesis of (R)-α- difluoromethyl-alanine and (S)-α-difluoromethyl-serine. Tetrahedron Asymmetry, 1996, 7, 2321-2332.
146. Jiang, Z.-X.; Liu, X.-P.; Qui, X.-L.; Qing, F.-L. Asymmetric synthesis of both enantiomers of syn-(3-trifluoromethyl)cysteine derivatives. J. Fluor. Chem., 2005, 126, 499-505.
147. Jiang, Z.-X.; Qing, F.-L. Regioselective and stereoselective nucleophilic ring opening of trifluoromethylated cyclic sulfates: Asymmetric synthesis of both enantiomers of syn-(3-trifluoromethyl)isoserine. J. Org. Chem., 2004, 69, 5486-5489.
148. Belokon, Y.N.; Maleev, V.I.; Savel'eva, T. F. Moskalenko, M. A.; Pripadchev, D. A.; Khrustalev, V. N. Saghiyan, A.S. Asymmetric synthesis of enantiomerically and diastereoisomerically enriched 4-[F or Br]-substituted glutamic acids. Amino Acids, 2010, 39, 1171-1176.
149. Taylor, P.P.; Pantaleone, D.P.; Senkpeil, R.F. Fotheringham I.G. Novel biosynthetic approaches to the production of unnatural amino acids using transaminases. TIBTECH, 1998, 16, 412-418.
150. Hong, E.Y.; Cha, M.H.; Yun, H.D. Kim B-G. Asymmetric synthesis of Ltert- leucine and L-3-hydroxyadamantylglycine using branched chain aminotransferase. J. Mol. Catal., B Enzym., 2010, 66, 228-233.
151. Bommarius, A.S.; Schwarm, M.; Drauz, K. Biocatalysis to amino acid-based chiral pharmaceuticals-examples and perspectives. J. Mol. Catal., B Enzym., 1998, 5, 1-11.
152. Altenbuchner, J.; Siemann-Herzberg, M. Hydantoinases and related enzymes as biocatalysts for the synthesis of unnatural chiral amino acids. Curr. Opin. Biotechnol., 2001, 12, 559-563.
153. Bommarius, A.S.; Drauz, K. An enzymatic route to L-ornithine from arginine-activation, selectivity and stabilization of L-arginase. Biorg. Med. Chem., 1994, 2, 617-626.
154. Shin, J.S.; Kim, B.G. Transaminase-catalyzed asymmetric synthesis of L-2- aminobutyric acid from achiral reactants. Biotechnol. Lett., 2009, 31, 1595-1599.
155. Baik, S-H.; Yoshioka, H. Enhanced synthesis of L-threo-3,4- dihydroxyphenylserine by high-density whole-cell biocatalyst of recombinant L-threonine aldolase from Streptomyces avelmitilis. Biotechnol. Lett., 2009, 31, 443-448.
156. Lecointe, L.; Rolland-Fulcrand, V.; Roumestant, M.L.; Viallefont, P.; Martinez, J. Chemoenzymatic synthesis of the two enantiomers of 7- azatryptophan. Tetrahedron Asymmetry, 1998, 9, 1753-1758.
157. Stella, S.; Chadha, A. Resolution of N-protected amino acid esters using whole cells of Candida parapsilosis ATCC 7330. Tetrahedron Asymmetry, 2010, 21, 457-460.
158. Kise Jr., K.J.; Bowler, B.E. Enantioselective synthesis of an unnatural bipyridyl amino acid and its incorporation into a peptide. Tetrahedron Asymmetry, 1998, 9, 3319-3324.
159. Zerkowski, J.A.; Hensley, L.M.; Abramowitz, D.M. Triazinyl-amino acids, new building blocks for pseudopeptides. Synlett, 2002, 29, 557-560.
160. Mann, E.; Kessler, H. New oxazole-based peptidomimetics: Useful building blocks for the synthesis of orthogonally protected macrocyclic scaffolds. Org. Lett., 2003, 5, 4567-4570.
161. Schwertfeger, H, Wüertele, C.; Serafin, M.; Hausmann, H.; Carlson, R.M.K.; Schreiner, P.R. Monoprotection of diols as a key step for the selective synthesis of unequally disubstituted diamondoids (nanodiamonds). J. Org. Chem., 2008, 73, 7789-7792.
162. Kuijpers, B.H.M.; Groothuys, S.; Keereweer, A.B.R.; Quaedflieg, P.J.L.M.; Blaauw, R.H.; van Delft, F.L.; Rutjes, F.P.J.T. Expedient synthesis of triazole-linked glycosyl amino acids and peptides. Org. Lett., 2004, 6, 3123-3126.
163. Kuijpers, B.H.M.; Groothuys, S.; Hawner, C.; ten Dam, J.; Quaedflieg, P.J.L.M.; Schoemaker, H.E.; van Delft, F.L.; Rutjes, F.P.J.T. Cu-catalyzed formation of triazole-linked glycoamino acids and application in chemoenzymatic peptide synthesis. Organic Process Research & Development, 2008, 12, 503-511.
164. Lane, J.W.; Halcomb, R.L. New design concepts for constraining glycosylated amino acids. Tetrahedron, 2001, 57, 6531-6538.
165. Balog, M.; Kálai, T.; Jeko, J. Synthesis of new conformationally rigid paramagnetic alpha-amino acids. Tetrahedron Lett., 2003, 44, 9213-9217.
166. Kálai, T.; Schindler, J.; Balog, M.; Fogassy, E.; Hideg, K. Synthesis and resolution of new paramagnetic alpha-amino acids. Tetrahedron, 2008, 64, 1094-1100.
167. Kruppa, M.; Imperato, G.; König, B. Synthesis of chiral amino acids with metal ion chelating side chains from L-serine using Negishi cross-coupling reaction. Tetrahedron, 2006, 62, 1360-1364.
168. Enes, R.F.; Tomé, A.C.; Cavaleiro, J.A. Synthesis of [60]fullerene-based alpha-amino acid derivatives. Tetrahedron, 2005, 61, 1423-1431.