Structural diversity of bicyclic amino acids

Amino Acids

Volumn 34, Issue 1, 2008, Pages 1-24

  Trabocchi, A ^a   Scarpi, D ^a   Guarna, A ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Drug design; Peptide; Peptidomimetic; Scaffold

Indexed keywords

2 AMINOCYCLOPENTANECARBOXYLIC ACID; 3,4 METHANOPROLINE; ALPHA AMINO ACID; AMINO ACID; BETA AMINO ACID; BICYCLIC AMINO ACID; BOWMAN BIRK INHIBITOR; CYCLOALKANE DERIVATIVE; DELTA AMINO ACID; EGLUMETAD; GAMMA AMINO ACID; LEWIS ACID; PEPTIDE; PEPTIDOMIMETIC AGENT; PIPECOLIC ACID; PROLINE DERIVATIVE; SPIROCYCLIC AMINO ACID; UNCLASSIFIED DRUG;

ALKYLATION; ALLYLATION; ASYMMETRIC SYNTHESIS; BIRCH REDUCTION; CATALYSIS; CLAISEN CONDENSATION; CURTIUS REARRANGEMENT; DIELS ALDER REACTION; DRUG DESIGN; HYDROGENOLYSIS; PAUSON KHAND REACTION; PRIORITY JOURNAL; REVIEW; RING CLOSING METATHESIS; STRUCTURE ANALYSIS;

ALKANES; AMINO ACIDS; AZA COMPOUNDS; CARBOHYDRATES; HETEROCYCLIC COMPOUNDS, 2-RING; HUMANS; SPIRO COMPOUNDS;

EID: 38149046540     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00726-007-0588-y     Document Type: Review

References (91)

1. AF Abdel-Magid JH Cohen CA Maryanoff 1999 Chemical process synthesis of β-amino acids and esters Curr Med Chem 6 955 970
2. Alcaide B, Sáez E (2005) Diastereoselective route to novel fused or bridged tricyclic β-lactams through intramolecular nitrone-alkene cycloaddition of 2-azetidinone-tethered alkenylaldehydes - synthetic applications to carbacephams and cyclic β-amino acid derivatives. Eur J Org Chem: 1680-1693
3. E Alonso F López-Ortuz C del Pozo E Peralta A Macías J González 2001 Spiro β-lactams as β-turn mimetics. Design, synthesis, and NMR conformational analysis J Org Chem 66 6333 6338
4. G Arnott J Clayden SD Hamilton 2006 Aza-bicyclic amino acids by stereoselective dearomatizing cyclisation of the enolates of N-nicotinoyl glycine derivatives Org Lett 8 5325 5328
5. D Arosio M Bertoli L Manzoni C Scolastico 2006 Click chemistry to functionalise peptidomimetics Tetrahedron Lett 47 3697 3700
6. A Basso L Banfi R Riva G Guanti 2005 A novel highly selective chiral auxiliary for the asymmetric synthesis of L- and D-α-amino acid derivatives via a multicomponent Ugi reaction J Org Chem 70 575 579
7. Belvisi L, Bernardi A, Manzoni L, Potenza D, Scolastico C (2000a) Conformational analysis of azabicycloalkane amino acid scaffolds as reverse-turn inducer dipeptide mimics. Eur J Org Chem: 2563-2569
8. Belvisi L, Gennari C, Madder A, Mielgo A, Potenza D, Scolastico C (2000b) Rationally designed bicyclic lactams control different turn motifs and folding patterns in hexapeptide mimics. Eur J Org Chem: 695-699
9. Belvisi L, Colombo L, Manzoni L, Potenza D, Scolastico C (2004) Design, synthesis, conformational analysis and application of azabicycloalkane amino acids as constrained dipeptide mimics. Synlett: 1449-1471
10. L Belvisi A Bernardi M Colombo L Manzoni D Potenza C Scolastico G Giannini M Marcellini T Riccioni M Castorina P Lo Giudice C Pisano 2006 Targeting integrins: insights into structure and activity of cyclic RGD pentapeptide mimics containing azabicycloalkane amino acids Bioorg Med Chem 14 169 180
11. JR Bencsik T Kercher M O'Sullivan JA Josey 2003 Efficient, Stereoselective synthesis of oxazolo[3,2-a]pyrazin-5-ones: novel bicyclic lactam scaffolds from the bicyclocondensation of 3-aza-1,5-ketoacids and amino alcohols Org Lett 5 2727 2730
12. 10) close to the experimentally derived bioactive conformation of NT(8-13) J Med Chem 47 5587 5590
13. Brackmann F, Colombo N, Cabrele C, de Meijere A (2006) An improved synthesis of 3,4-(aminomethano)proline and its incorporation into small oligopeptides. Eur J Org Chem: 4440-4450
14. Bravin FM, Busnelli G, Colombo M, Gatti F, Manzoni L, Scolastico C (2004) Synthesis of conformationally restricted and optically pure analogues of serine-proline dipeptide via aldol condensation. Synthesis: 353-358
15. E Buñuel AM Gil MD Díaz-De-Villegas C Cativiela 2001 Synthesis of constrained prolines by Diels-Alder reaction using a chiral unsaturated oxazolone from (R)-glyceraldehyde as starting material Tetrahedron 57 6417 6427
16. D Casabona C Cativiela 2006 Efficient synthesis of a new pipecolic acid analogue with a bicyclic structure Tetrahedron 62 10000 10004
17. LL Chang Q Truong GA Doss M MacCoss K Lyons E McCauley R Mumford G Forrest S Vincent JA Schmidt WK Hagmann 2007 Highly constrained bicyclic VLA-4 antagonists Bioorg Med Chem Lett 17 597 601
18. WH Chiou N Mizutani I Ojima 2007 Highly efficient synthesis of azabicyclo[x.y.0]alkane amino acids and congeners by means of Rh-catalyzed cyclohydrocarbonylation J Org Chem 72 1871 1882
19. DC Cole 1994 Recent stereoselective synthetic approaches to β-amino acids Tetrahedron 50 9517 9582
20. P Conti M De Amici S Joppolo di Ventimiglia TB Stensbøl U Madsen H Bräuner-Osborne E Russo G De Sarro G Bruno C De Micheli 2003 Synthesis and anticonvulsant activity of novel bicyclic acidic amino acids J Med Chem 46 3102 3108
21. FM Cordero F Pisaneschi K Meschini Batista S Valenza F Machetti A Brandi 2005 A new bicyclic dipeptide isostere with pyrrolizidinone skeleton J Org Chem 70 856 867
22. J Czombos W Aelterman A Tkachev JC Martins D Tourwé A Péter G Tóth F Fülöp N De Kimpe 2000 Convenient synthesis of 3,4-methano-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and its derivatives as doubly constrained nonproteinogenic amino acid derivatives J Org Chem 65 5469 5475
23. Danieli E, Trabocchi A, Menchi G, Guarna A (2005) Synthesis of glycidol- and sugar-derived bicyclic β- and γ/δ-amino acids for peptidomimetic design. Eur J Org Chem: 4372-4381
24. DE Davies PM Doyle RD Farrant RD Hill PB Hitchcock PN Sanderson DW Young 2003 Synthesis of an external β-turn based on the GLDV motif of cell adhesion proteins Tetrahedron Lett 44 8887 8891
25. C Dominguez L Prieto MJ Valli SM Massey M Bures RA Wright BG Johnson SL Andis A Kingston DD Schoepp JA Monn 2005 Methyl substitution of 2-aminobicyclo[3.1.0]hexane 2,6-dicarboxylate (LY354740) determines functional activity at metabotropic glutamate receptors: identification of a subtype selective mGlu2 receptor agonist J Med Chem 48 3605 3612
26. PS Dragovich R Zhou TJ Prins 2002 Synthesis of an optically active, bicyclic 2-pyridone dipeptide mimetic J Org Chem 67 741 746
27. HME Duggan PB Hitchcock DW Young 2005 Synthesis of 5/7-, 5/8- and 5/9-bicyclic lactam templates as constraints for external β-turns Org Biomol Chem 3 2287 2295
28. 7 integrin antagonists Bioorg Med Chem Lett 14 591 596
29. 7 integrin receptor antagonists Bioorg Med Chem 13 6693 6702
30. MA Estiarte M Rubiralta A Diez 2000 Oxazolopiperidin-2-ones as Type II β-turn mimetics: synthesis and conformational analysis J Org Chem 65 6992 6999
31. J Gante 1994 Peptidomimetics-tailored enzyme inhibitors Angew Chem Int Ed Engl 33 1699 1720
32. J Gardiner AD Abell 2003 A diastereoselective synthesis of the tetrahydropyridazinone core of 2-oxo-1,6-diazobicyclo[4.3.0]nonane-9- carboxylate-based peptidimimetics starting from (S)-phenylalanine Tetrahedron Lett 44 4227 4230
33. SH Gellman 1998 Foldamers: a manifesto Acc Chem Res 31 173 180
34. A Giannis T Kolter 1993 Peptidomimetics for receptor ligands-discovery, development, and medical perspectives Angew Chem Int Ed Engl 32 1244 1267
35. γ of the side chain Tetrahedron Asymmetr 16 3115 3123
36. OO Grygorenko OS Artamonov GV Palamarchuk RI Zubatyuk OV Shishkin IG Komarov 2006 Stereoselective synthesis of 2,4-methanoproline homologues Tetrahedron Asymmetr 17 252 258
37. X Gu X Tang S Cowell J Ying VJ Hruby 2002 A novel strategy toward [6,5]-bicyclic β-turn dipeptide Tetrahedron Lett 43 6669 6672
38. X Gu S Cowell J Ying X Tang VJ Hruby 2003 Synthesis of β-phenyl-δ, β-unsaturated amino acids and stereoselective introduction of side chain groups into [4,3,0]-bicyclic β-turn dipeptides Tetrahedron Lett 44 5863 5866
39. [2,3]-Leu-enkephalin analogues Org Lett 6 3285 3288
40. M Günter HJ Gais 2003 Asymmetric synthesis of fused bicyclic α-amino acids having a hexahydro-cyclopenta[c]pyridine skeleton via intramolecular Pauson-Khand reaction of 1-sulfonimidoyl-substituted 5-azaoct-1-en-7-ynes J Org Chem 68 8037 8041
41. Haberhauer G, Rominger F (2003) Straightforward synthesis of a novel class of rigid bicyclic dipeptidomimetics from simple dipeptides: fused imidazole amino acids. Synlett: 780-784
42. 3 receptor ligands J Med Chem 46 3883 3899
43. L Halab JAJ Becker Z Darula D Tourwé BL Kieffer F Simoni WD Lubell 2002 Probing opioid receptor interactions with azacycloalkane amino acids. Synthesis of a potent and selective ORL1 anatagonist J Med Chem 45 5353 5357
44. S Hanessian Luo X R Schaum S Michnick 1998 Design of secondary structures in unnatural peptides: stable helical γ-tetra-, hexa-, and octapeptides and consequences of α-substitution J Am Chem Soc 120 8569 8570
45. S Hanessian H Sailes A Munro E Therrien 2003 Synthesis of diversely functionalized indolizidinones and related bicyclic lactams using intramolecular Grubbs olefin metathesis and Dieckmann condensation J Org Chem 68 7219 7233
46. PW Harris MA Brimble PD Gluckman 2003 Synthesis of cyclic proline-containing peptides via ring-closing metathesis Org Lett 5 1847 1850
47. K Hattori RB Grossman 2003 Functionalized cis- and trans-fused bicyclic α-amino acids via stereoselective double annulation and dequaternization reactions J Org Chem 68 1409 1417
48. T Hintermann K Gademann B Jaun D Seebach 1998 Gamma-peptides forming more stable secondary structures than alpha-peptides: synthesis and helical NMR-solution structure of the gamma-hexapeptide analog of H-(Val-Ala-Leu)(2)-OH Helv Chim Acta 81 983 1002
49. BL Iverson 1997 Betas are brought into the fold Nature 385 113 115
50. G Jeannotte WD Lubell 2004 Synthesis of fused heteroarylprolines and pyrrolopyrroles J Org Chem 69 4656 4662
51. B Jiang M Xu 2002 Catalytic diastereoselective Pauson-Khand reaction: an efficient route to enantiopure cyclopenta[c]proline derivatives Org Lett 4 4077 4080
52. E Juaristi H Lopez-Ruiz 1999 Recent advances in the enantioselective synthesis of β-amino acids Curr Med Chem 6 983 1004
53. S Koep HJ Gais G Raabe 2003 Asymmetric synthesis of unsaturated fused bicyclic proline analogues through amino alkylation of cyclic bis(allylsulfoximine)titanium complexes and migratory cyclization of δ-amino alkenyl aminosulfoxonium salts J Am Chem Soc 125 13243 13251
54. F Köhler HJ Gais G Raabe 2007 Asymmetric synthesis of highly substituted γ-amino acids from allyltitanium sulfoximines Org Lett 9 1231 1234
55. Lalli C, Trabocchi A, Guarna F, Mannino C, Guarna A, (2006) Synthesis of a bicyclic proline analogue from L-ascorbic acid. Synthesis: 3122-3126
56. P Langer H Kählig K Zierler-Gould JW Bats J Mulzer 2002 A bicyclic cispentacin derivative as a novel reverse turn inducer in a GnRH mimetic J Org Chem 67 6878 6883
57. C Lescop L Mévellec F Huet 2001 A new synthesis of 2-azabicyclo[2.1.1]hexanes J Org Chem 66 4187 4193
58. YT Liu JK Wong M Tao R Osterman M Sannigrahi VM Girijavallabhan A Saksena 2004 Carboxy mediated stereoselective reduction of ketones with sodium triacetoxyborohydride: synthesis of novel 3,4-fused tetrahydropyran and tetrahydrofuran prolines Tetrahedron Lett 45 6097 6100
59. F Machetti A Ferrali G Menchi EG Occhiato A Guarna 2000 Oligomers of enantiopure bicyclic γ/δ-amino acids (BTAa). 1. Synthesis and conformational analysis of 3-aza-6,8-dioxabicyclo[3.2.1]octane-7-carboxylic acid oligomers (PolyBTG) Org Lett 2 3987 3990
60. S Maechling SE Norman JE McKendrick S Basra K Köppner S Blechert 2006 Ring-rearrangement metathesis of bicyclic amino acid derivatives Tetrahedron Lett 47 189 192
61. Maison W, Grohs DC, Prenzel AHGP (2004) Efficient synthesis of structurally diverse diazabicycloalkanes: scaffolds for modular dipeptide mimetics with tunable backbone conformations. Eur J Org Chem: 1527-1543
62. PK Mandal KK Kaluarachchi D Ogrin SG Bott JS McMurray 2005 An efficient synthesis of the constrained peptidomimetic 2-oxo-3-(N-9- fluorenyloxycarbonylamino)-1-azabicyclo[4.3.0]nonane-9-carboxylic acid from pyroglutamic acid J Org Chem 70 10128 10131
63. S Manku DP Curran 2005 Fluorus mixture synthesis of 4-alkylidene cyclopentenones via a rhodium-catalyzed [2 + 2 + 1] cycloaddition of alkynyl allenes J Comb Chem 7 63 68
64. Manzoni L, Belvisi L, Di Carlo E, Forni A, Invernizzi D, Scolastico C (2006) Synthesis of functionalized azabicycloalkane amino acids as dipeptide mimics. Synthesis: 1133-1140
65. R Millet J Domarkas P Rombaux B Rigo R Houssin JP Hénichart 2002 Synthesis of an azabicycloalkane amino acid scaffold as potential rigid dipeptide mimetic Tetrahedron Lett 43 5087 5088
66. C Mouriès B Deguin F Lamari MJ Foglietti F Tillequin M Koch 2003 Homochiral rigid γ-amino acid glycosides from aucubin Tetrahedron Asymm 14 1083 1086
67. Y Otani S Futaki T Kiwada Y Sugiura A Muranaka N Kobayashi M Uchiyama K Yamaguchi T Ohwada 2006 Oligomers of β-amino acid bearing non-planar amides form ordered structures Tetrahedron 62 11635 11644
68. Peri F, Cipolla L, La Ferla B, Nicotra F (2000) Synthesis of bicyclic sugar azido acids and their incorporation in cyclic peptides. Chem Commun: 2303-2304
69. F Polyak WD Lubell 2001 Mimicry of peptide backbone geometry and heteroatomic side-chain functionality: synthesis of enantiopure indolizidin-2-one amino acids possessing alcohol, acid, and azide functional groups J Org Chem 66 1171 1180
70. W Qiu X Gu VA Soloshonok MD Carducci VJ Hruby 2001 Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics Tetrahedron Lett 42 145 148
71. MHV Ramana Rao E Pinyol WD Lubell 2007 rigid dipeptide mimics: synthesis of enantiopure C6-functionalized pyrrolizidinone amino acids J Org Chem 72 736 743
72. Rammeloo T, Stevens CV (2002) A new and short method for the synthesis of 2,4-methanoproline. Chem Commun: 250-254
73. T Rammeloo CV Stevens N De Kimpe 2002 Synthesis of 2,4-methanoproline analogues via an addition-intramolecular substitution sequence J Org Chem 67 6509 6513
74. M Salvati FM Cordero F Pisaneschi F Bucelli A Brandi 2005 New developments in the synthesis of pyrrolizidinone-based dipeptide isosteres Tetrahedron 61 8836 8847
75. D Scarpi EG Occhiato A Trabocchi RJ Leatherbarrow ABE Brauer M Nievo A Guarna 2001 Introduction of the new dipeptide isostere 7-endo-BtA as reverse turn inducer in a Bowman-Birk proteinase inhibitor: synthesis and conformational analysis Bioorg Med Chem 9 1625 1632
76. Seebach D, Matthews JL (1997) β-Peptides: a surprise at every turn. Chem Commun: 2015-2022
77. N Sewald 1996 Stereoselective synthesis of β-amino acids via conjugate addition of nitrogen nucleophiles to α,β-unsaturated esters. Recent advances Amino Acids 11 397 408
78. JP Strachan RC Whitaker CH Miller BS Bhatti 2006 Synthesis of bicyclic tertiary α-amino acids J Org Chem 71 9909 9911
79. H Sun C Martin D Kesselring R Keller KD Moeller 2006 Building functionalized peptidomimetics: use of electroauxiliaries for introducing N-acyliminium ions into peptides J Am Chem Soc 128 13761 13771
80. L Szabo BL Smith KD McReynolds AL Parrill ER Morris J Gervay 1998 Solid phase synthesis and secondary structural studies of (1->5)-amide linked sialooligomers J Org Chem 63 1074 1078
81. VI Tararov R Kadyrov Z Kadyrova N Dubrovina A Börner 2002 An improved synthesis of enantiopure 2-azabicyclo[2.2.1]heptane-3-carboxylic acid Tetrahedron Asymm 13 25 28
82. 8 region J Org Chem 65 2484 2493
83. A Trabocchi N Cini G Menchi A Guarna 2003 A new bicyclic proline-mimetic amino acid Tetrahedron Lett 44 3489 3492
84. Trabocchi A, Menchi G, Guarna F, Machetti F, Scarpi D, Guarna A (2006) Design, synthesis, and applications of 3-aza-6,8-dioxabicyclo[3.2.1]octane-based scaffolds for peptidomimetic chemistry. Synlett: 331-353
85. A Trabocchi EG Occhiato D Potenza A Guarna 2002 Synthesis and conformational analysis of small peptides containing 6-endo-BT(t)L scaffolds as reverse turn mimetics J Org Chem 67 7483 7492
86. N Valls M López-Canet M Vallribera J Bonjoch 2001 First total syntheses of aeruginosin 298-A and aeruginosin 298-B, based on a stereocontrolled route to the new amino acid 6-hydroxyoctahydroindole-2- carboxylic acid Chem Eur J 7 3446 3460
87. RM van Well MEA Meijer HS Overkleeft JH van Boom GA van der Marel M Overhand 2003 Synthesis of bridged sugar amino acids: a new entry into conformationally locked δ- and β-amino acids Tetrahedron 59 2423 2434
88. W Wang J Yang J Ying C Xiong J Zhang C Cai VJ Hruby 2002 Stereoselective synthesis of dipeptide β-turn mimetics: 7-benzyl and 8-phenyl substituted azabicyclo[4.3.0]nonane amino acid esters J Org Chem 67 6353 6360
89. BV Yang LM Doweyko 2005 Highly regioselective Diels-Alder reactions of 9-substituted anthracenes and 2-acetamidoacrylate: synthesis of conformationally constrained α-amino acids Tetrahedron Lett 46 2857 2860
90. SJ Yeo KS Jeong H Han J Kim N Jeong 2006 β-Amino acids based on bicyclic skeleton: bicyclo[3.3.0]octane-5-amino-1-carboxylic acids Tetrahedron Lett 47 7389 7393
91. J Zhang C Xiong W Wang J Ying VJ Hruby 2002 Stereoselective bromination-Suzuki cross-coupling of dehydroamino acids to form novel reverse-turn peptidomimetics: substituted unsaturated and saturated indolizidinone amino acids Org Lett 4 4029 4032