Syntheses of optically active 2-amino-4-oxobutyric acid and N,O-protected derivatives

Amino Acids

Volumn 16, Issue 3-4, 1999, Pages 251-272

  Meffre, P ^a,b  

^a Ecole Natl Supericure de C   (France)

^b Ecole Natl Superieure de C   (France)

Author keywords

semialdehyde; 2 Amino 4 oxobutyric acid; Amino acids; Aspartaldehyde; Aspartic acid; Enantioselective synthesis; Unusual amino acids

Indexed keywords

ALDEHYDE DERIVATIVE; ALLYLGLYCINE; ASPARTIC ACID; BUTYRIC ACID DERIVATIVE; HOMOSERINE; METHIONINE;

AMINO ACID SYNTHESIS; PRIORITY JOURNAL; REVIEW;

AMINO ACIDS; ASPARTIC ACID; STEREOISOMERISM;

EID: 0032970032     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF01388171     Document Type: Review

References (111)

1. Agami C, Couty F, Poursoulis M (1992) Aza-Cope rearrangement. Asymmetric syntheses of α-amino acids: (R)-homoserine lactone and (R,R)-4-(1-hydroxy-1-methylethyl)proline. Synlett: 847-848
2. Agami C, Couty F, Lin J, Mikaeloff A, Pousoulis M (1993) Asymmetric synthesis of α-amino acids via cationic aza-Cope rearrangements. Tetrahedron 49: 7239-7250
3. Albertson NF (1946) The synthesis of amino acids from ethyl acetamidomalonate and ethyl acetamidocyanoacetate. III. The use of primary halides. J Am Chem Soc 68: 450-453
4. Baldwin JE, Flinn A (1987) Use of L-aspartic acid β-semialdehyde in the synthesis of more compex non protein amino acids. Tetrahedron Lett 28: 3605-3608
5. Baldwin JE, Lee E (1986) Synthesis of bicyclic γ-lactams via oxazolidinones. Tetrahedron 42: 6551-6554
6. Baldwin JE, Lowe C, Schofield CJ, Lee E (1986) A γ-lactam analogue of penems possessing antibacterial activity. Tetrahedron Lett 27: 3461-3464 and 5042
7. Baldwin JE, North M, Flinn A (1987) A convenient new synthesis of homoserine lactone. Tetrahedron Lett 28: 3167-3168
8. Baldwin JE, Norris WJ, Freeman RT, Bradley M, Adlington RM, Long-Fos S, Schofield CJ (1988a) γ-Lactam formation from tripeptides with isopenicillin N synthase. J Chem Soc Chem Com: 1128-1130
9. Baldwin JE, North M, Flinn A (1988b) Synthesis and rearrangement of homoserine derivatives. Tetrahedron 44: 637-642
10. Baldwin JE, Freeman RT, Schofield C (1989a) Synthesis of a novel bicyclic γ-lactam analogue of the 1-oxapenams. Tetrahedron Lett 30: 4019-4020
11. Baldwin JE, Freeman RT, Lowe C, Schofield CJ, Lee E (1989b) A γ-lactam analogue of the penems possessing antibacterial activity. Tetrahedron 45: 4537-4550
12. Barrett GC (1985) Chemistry and biochemistry of the amino acids. In: Barrett GC (ed) Chapman and Hall, London New York, pp 246-296
13. Ben-Bari M, Dewynter G, Aymard C, Jei T, Montero J-L (1995) Synthèse de dérivés phosphonylés de l'acide aspartique inhibiteurs potentiels de l'ATCase. Phosphorus, Sulfur and Silicon 105: 129-144
14. Bergmeier SC, Cobas AA, Rapoport H (1993) Chirospecific synthesis of (1S, 3R)-1-amino-3-(hydroxymethyl)cyclopentane, precursor for carbocyclic nucleoside synthesis. Dieckmann cyclisation with an α-amino acid. J Org Chem 58: 2369-2376
15. Black S, Wright NG (1955a) β-Aspartokinase and β-aspartyl phosphate. J Biol Chem 213: 27-38
16. Black S, Wright NG (1955b) Aspartic β-semialdehyde dehydrogenase and aspartic β-semialdehyde. J Biol Chem 213: 39-50
17. Black S, Wright NG (1955c) Homoserine dehydrogenase. J Biol Chem 213: 51-60
18. Blickling S, Renner C, Laber B, PohlenzH-D, Holak TA, Huber R (1997) Reaction mechanism of Escherichia coli dihydrodipicolinate synthase investigated by X-ray crystallography and NMR spectroscopy. Biochemistry 36: 24-33
19. Bold G, Steiner H, Moesch L, Walliser B (1990) Herstellung von "Semialdehyd"-Derivaten von Asparaginsäure-und Glutaminsäure durch Rosenmund-Reduktion. Helv Chim Acta 73: 405-410
20. Bratusek U, Kejzar I, Svete J, Stanovnik B (1996) The synthesis of N-phthaloylazatryptophane derivatives. Acta Chim Slov 43: 105-117
21. Bubert C, Voigt J, Biasetton S, Reiser O (1994) A new approach to β- and γ-amino esters and amino aldehydes by regioselective ozonolysis of 2,3-dihydropyrroles and 1,2,3,4-tetrahydropyridines. Synlett: 675-677
22. Burger K, Rudolph M, Fehn S, Worku A, Gobulev A (1995) Application of hexafluoroacetone as protecting and activating reagent in amino acid and peptide chemistry. Amino Acids 8: 195-199
23. Cannarsa MJ (1996) Single enantiomer drugs: new strategies and directions. Chem Ind: 374-378
24. Cavrini V, Chiarini A, Garuti L, Giovanninetti G, Franchi L (1976) Riceche su sostanze ad attivita antivirale. Nota V - analoghi strutturali dell'arginina. Farmaco Ed Sci 31: 599-606
25. Chang MNT, Walsh CT (1981) Stereochemical analysis of γ-replacement and γ-elimination processes catalyzed by a pyridoxal phosphate dependent enzyme. J Am Chem Soc 103: 4921-4927
26. Chauvel EN, Llorens-Cortes C, Coric P, Wilk S, Roques BP, Fournié-Zaluski M-C (1994) Differential inhibition of aminopeptidase A and aminopeptidase N by new β-amino thiols. J Med Chem 37: 2950-2957
27. Cooper RDG, Jose F, McShane L, Koppel GA (1978) A chiral synthesis of D-homoserine and its application to the synthesis of nocardicin A. Tetrahedron Lett: 2243-2246
28. Coppola GM (1987) Asymmetric synthesis: construction of chiral molecules using amino acids. John Wiley and Sons, New York
29. Coulter CV, Gerrard JA, Kraunsoe JAE, Moore DJ, Pratt AJ (1996) (S)-Aspartate semialdehyde: synthetic and stuctural studies. Tetrahedron 52: 7127-7136
30. Cox RJ, Sherwin WA, Lam LKP, Vederas JC (1996) Synthesis and evaluation of novel substrates and inhibitors of N-succinyl-L,L-diaminopimelate aminotransferase (DAP-AT) from Escherichia coli. J Am Chem Soc 118: 7449-7460
31. Crosby J (1992) Chirality in industry: the commercial manufacture and applications of optically active compounds, vol 1. In: Collins AN, Sheldrake GN, Crosby J (eds) John Wiley and Sons, Chichester, pp 1-66
32. Crosby J (1997) Chirality in industry II: developments in the manufacture and applications of optically active compounds, vol 2. In: Collins AN, Sheldrake GN, Crosby J (eds) John Wiley and Sons, Chichester, pp 1-10
33. 19F NMR spectroscopy. J Org Chem 54: 2420-2425
34. David S, Veyrieres A (1970) Synthesis of 3-amino-2,3-dideoxytetrose derivatives. Carbohyd Res 13: 203-209
35. Davies IW, Reider PJ (1996) Practical asymmetric synthesis. Chem Ind: 412-415
36. De la Figuera N, Rozas I, Garcia-Lopez MT, Gonzales-Muniz R (1994) 2(S)-Amino-3-oxo-11b(R)-hexahydroindolizino[8,7-b]indole-5(S)-carboxylate as a new type of β-turn dipeptide mimetic. J Chem Soc Chem Commun: 613-614
37. De la Figuera N, Alkorta I, Garcia-Lopez MT, Herranz R, Gonzales-Muniz R (1995) 2-Amino-3-oxohexahydroindolizino[8,7-b]indole-5-carboxylate derivatives as new scaffolds for mimicking β-turn secondary structures. Molecular dynamics and stereoselective synthesis. Tetrahedron 51: 7841-7856
38. Dehmlow EV, Westerheide R (1993) A new simple route to N,O-protected (S)-2-amino-4-oxobutyric acid. Synthesis: 1225-1226
39. Duthaler RO (1994) Recent developments in the stereoselective synthesis of α-amino acids. Tetrahedron 50: 1539-1650
40. Easton CJ, Hutton CA (1998) Recent developments in the use of N-phthaloyl-amino acid derivatives in synthesis. Synlett: 457-466
41. Emmer G, Grassberger MA, Schulz G, Boesch D, Gavériaux C, Loor F (1994) Derivatives of a novel cyclopeptolide. 2. Synthesis, activity against multidrug resistance in CHO and KB cells in vitro, and structure-activity relationships. J Med Chem 37: 1918-1928
42. Faust J, Schreiber K (1989) Der Normalisierungsfaktor für die Tomatenmutante Chloronerva: Synthese des (S)-Piperidin-2-Carbonsäureanalogons von Nicotianamin. Z Chem 29: 20-21
43. Faust J, Preiss A, Shreiber K, Ripperger H (1983) On the "normalizing" factor for the tomato mutant chloronerva-XIV: synthesis of the proline analogue of the phytosiderophore nicotianamine. Tetrahedron 39: 1593-1596
44. Faust J, Schreiber K, Ripperger H (1984) Der "Normalisierungsfaktor" für die Tomatenmutante Chloronerva: ein einfacher Zugang zum "Aldehydbaustein" der Nicotianaminesynthese. Z Chem 24: 330-331
45. Fushiya S, Nakatsuyama S, Sato Y, Nozoe S (1981a) Synthesis of nicotianamine and related compound, derivatives of azetidine-2-carboxylic acid. Heterocycle 15: 819-822
46. Fushiya S, Sato Y, Nakatsuyama S, Kanuma N, Nozoe S (1981b) Synthesis of avenic acid A and 2′-deoxymugineic acid, amino acids possessing an iron chelating activity. Chem Lett: 909-912
47. Fushiya S, Maeda K, Funayama T, Nozoe S (1988a) 4-N-Hydroxy-L-2,4-diaminobutyric acid. A strong inhibitor of glutamine synthetase. J Med Chem 31: 480-483
48. Fushiya S, Watari F, Tashiro T, Kuzano G, Nozoe S (1988b) A new acidic amino acid from a basidiomycetes, lactarius piperatus. Chem Pharm Bull 36: 1366-1370
49. Gao Y, Lane-Bell P, Vederas JC (1998) Stereoselective synthesis of meso-2,6-diaminopimelic acid and its selectively protected derivatives. J Org Chem 63: 2133-2143
50. Garvey DS, May PD, Nadzan AM (1990) 3,4-Disubstituted γ-lactam rings as conformationally constrained mimics of peptide derivatives containing aspartic acid or norleucine. J Org Chem 55: 936-940
51. 6-hydroxylysine. Tetrahedron Lett 34: 1159-1162
52. Geze M, Blanchard P, Fourrey JL, Robert-Gero M (1983) Synthesis of sinefungin and its C-6′ epimer. J Am Chem Soc 105: 7638-7640
53. Giorgianni F, Beranova S, Wesdemiotis C, Viola RE (1995) Elimination of the sensitivity of L-aspartase to active-site-directed inactivation without alteration of catalytic activity. Biochemistry 34: 3529-3535
54. Girard A, Greek C. Genêt JP (1998) Rapid syntheses of 3-amino-5-hydroxymethyl-γ-lactones from L-allylglycine. Tetrahedron Lett 39: 4259-4260
55. Hanessian S, Yang R-J (1996) The asymmetric synthesis of allylglycine and other unnatural α-amino acids via zinc-mediated allylation of oximes in aqueous media. Tetrahedron Lett 37: 5273-5276
56. Hoffmann MG, Zeiss H-J (1992) A novel and convenient route to L-homoserine lactones and L-phosphinothricin from L-aspartic acid. Tetrahedron Lett 33: 2669-2672
57. 2-modified RA-VII derivatives. Chem Pharm Bull 41: 1402-1410
58. Jungheim LN, Boyd DB, Indelicato JM, Pasini CE, Preston D, Alborn WE (1991) Synthesis, hydrolysis rates, supercomputer modeling, and antibacterial activity of bicyclic tetrahydropyridazinones. J Med Chem 34: 1732-1739
59. Katagiri N, Okada M, Kaneko C, Furuya T (1996) Synthesis of chiral cyclic nitrones via a nitrosoketene intermediate and their use for the complete EPC synthesis of nonproteinogenic amino acids. Tetrahedron Lett 37: 1801-1804
60. Kazmaier U (1996) Synthesis of γ,δ-unsaturated amino acids via ester enolate Claisen rearrangement of chelated allylic esters. Amino Acids 11: 283-299
61. Keith DD, Tortora JA, Ineichen K, Leimgruber W (1975) The total synthesis of rhizobitoxine. Tetrahedron 31: 2633-2636
62. Keith DD. Tortora JA, Yang R (1978) Synthesis of L-2-amino-4-methoxy-trans-but-3-enoic acid. J Org Chem 43: 3711-3713
63. Knapp S, Hale JJ, Bastos M, Molina A, Chen KY (1992) Synthesis of hypusine and other polyamines using dibenzyltriazones for amino protection. J Org Chem 57: 6239-6256
64. Koch T, Buchardt O (1993) Synthesis of L-(+)-selenomethionine. Synthesis: 1065 1067
65. Kokotos G, Padron JM, Martin T, Gibbons WA, Martin VS (1998) A general approach to the asymmetric synthesis of unsaturated lipidic α-amino acids. The first synthesis of α-amino arachidonic acid. J Org Chem (in press)
66. Matsuura F, Hamada Y, Shioiri T (1994a) Total syntheses of phytosiderophores, 3-epi-hydroxymugineic acid, distichonic acid A, and 2′-hydroxynicotianamine. Tetrahedron 50: 265-274
67. Matsuura F, Hamada Y, Shioiri T (1994b) Total synthesis of 2′-deoxymugineic acid and nicotianamine. Tetrahedron 50: 9457-9470
68. Meffre (1998) In different reaction conditions, this strategy may lead to the formation of vinylsulfide in good yield. Synthesis (submitted to publication)
69. Meffre P, Lhermitte H, Vo-Quang L, Vo-Quang Y, Le Goffic F (1991) A new class of unusual α-amino acids: α-amino acid β,γ-enol thioethers. Tetrahedron Lett 32: 4717-4720
70. Meffre P, Durand P, Le Goffic F (1995) Straightforward synthesis of optically pure methyl (S)-2-phthalimido-4-oxobutanoate. Synthesis: 1111-1114
71. Meffre P, Durand P, Le Goffic F (1999) Methyl (S)-2-phthalimido-4-oxobutanoate. Org Synth 76 (in press)
72. Metzler DE (1977) Biochemistry: the chemical reactions of living cells. Academic Press Inc, New York. p 824
73. Mock GA, Moffatt JG (1982) An approach to the total synthesis of sinefungin. Nucleic Acid Res 10: 6223-6234
74. Myers AG, Gleason JL, Yoon T, Kung DW (1997) Highly practical methodology for the synthesis of D- and L-α-amino acids, N-protected α-amino acids, and N-methyl-α-amino acids. J Am Chem Soc 119: 656-673
75. Neuberger A, Tait GH (1962) Synthesis of L-aspartic β-semialdehyde. J Chem Soc: 3963 3968
76. Ohfune Y, Nomoto K (1981) Synthesis of (+)-avenic acid A. Chem Lett: 827-828
77. Ohfune Y, Tomita M, Nomoto K (1981) Total synthesis of 2′-deoxyugineic acid, the metal chelator excreted from wheat root. J Am Chem Soc 103: 2409-2410
78. Oida F, Ota N, Mino Y, Nomoto K, Sugiura Y (1989) Stereospecific iron uptake mediated by phytosiderophore in gramineous plants. J Am Chem Soc 111: 3436-3437
79. Ornstein PL, Melikian A, Martinelli MJ (1994) Intramolecular Diels - Alder route to 6-oxodecahydroisoquinoline-3-carboxylates: intermediates for the synthesis of conformationally constrained excitatory amino acid antagonists. Tetrahedron Lett 35: 5759-5762
80. Pellegrini M, Weitz IS, Chorev M, Mierke DF (1997) A trisubstituted 1,4-diazepine-3-one-based dipeptidomimetic: conformational characterization by NMR and computer simulation. J Am Chem Soc 119: 2430-2436
81. 2)-OH}. Synlett: 595-596
82. 2)-OH. Int J Peptide Protein Res 44: 288-294
83. Ramalingam K, Woodward RW (1988) Synthesis of stereospecific deuterium-labeled homoserines and homoserine lactones. J Org Chem 53: 1900-1903
84. Ramsamy K, Olsen RK, Emery T (1982) Synthesis of N-t-Boc-L-α-aminoadipic acid 1-t-butyl 6-ethyl ester from L-aspartic acid: a new route to L-α-aminoadipic acid. Synthesis: 42-43
85. Richards A, McCague R (1997) The impact of chiral technology on the pharmaceutical industry. Chem Ind: 422-425
86. Ripperger H (1988) Synthesis of 3,4-seconicotianamine. J Prakt Chem 330: 470-472
87. Robl JA, Karanewsky DS, Asaad MM (1995) Synthesis of benzo-fused, 7,5- and 7,6-fused azepinones as conformationally restricted dipeptide mimetics. Tetrahedron Lett 36: 1593-1596
88. Schindler JF, Viola RE (1994) Mechanism-based inactivation of L-aspartase from Escherichia coli. Biochemistry 33: 9365-9370
89. Shioiri T, Irako N, Sakakibari S, Matsuura F, Hamada Y (1997) A new efficient synthesis of nicotianamine and 2′-deoxymugineic acid. Heterocycles 44: 519-530
90. Shono T, Matsumura Y, Tsubata K, Sugihara Y, Yamane S-I, Kanazawa T, Aoki T (1982) Electroorganic chemistry. 60. Electroorganic synthesis of enamides and ene-carbamates and their utilization in organic synthesis. J Am Chem Soc 104: 6697-6703
91. Stockman RA, Szeto P, Thompson SHJ, Hadley MS, Lathbury DC, Gallagher T (1996) Synthesis of functionalised azabicycles via a regiospecific intramolecular aldol reaction. Synlett: 853-855
92. 2. J Med Chem 36: 2356-2361
93. Svete J, Stanovnic B, Tisler M (1994) The synthesis of azatryptophane derivatives. J Heterocyclic Chem 31: 1259-1266
94. Szeto P, Lathbury DC, Gallagher T (1995) Heterocyclic ketones as pre-formed building blocks. Synthesis of (-)-slaframine. Tetrahedron Lett 36: 6957-6960
95. Tong G, Perich JW, Johns RB (1990) Synthesis of Leu-Abu(P)and Glu-Abu(P)-Leu. Isosteres of Ser(P)-Peptides. Tetrahedron Lett 31: 3759-3762
96. 2)-OH and its use for the facile synthesis of Glu-Abu(P)-Leu. Aust J Chem 45: 1225-1240
97. Toujas JL, Jost E, Vaultier M (1997) Synthesis of homochiral N-Boc-β-aminoaldehydes from N-Boc-β-aminonitriles. Bull Soc Chim Fr 134: 713-717
98. 2H] methionine in norcardicin A biosynthesis. J Chem Soc Chem Com: 1579-1581
99. Tudor DW, Lewis T, Robins DJ (1993) Synthesis of the trifluoroacetate salt of aspartic acid β-semialdehyde, an intermediate in the biosynthesis of L-lysine, L-threonine, and L-methionine. Synthesis: 1061-1062
100. Uzar HC (1991) Improved synthesis of L-homoserine derivatives from L-aspartic acid. Synthesis: 526-528
101. Valerio RM, Alewood PF, Johns RB (1988) Synthesis of optically active 2-tertbutyloxycarbonylamino)-4-dialkoxyphosphorylbutanoate protected isosteres of ophosphoserine for peptide synthesis. Synthesis: 786-789
102. Venkatraman S, Roon RJ, Schulte MK, Koerner JF, Johnson RL (1994) Synthesis of oxadiazolidinedione derivatives as quisqualic acid analogues and their evaluation at a quisqualate-sensitized site in the rat hippocampus. J Med Chem 37: 3939-3946
103. Walsh C (1982) Suicide substrate: mechanism-based enzyme inactivators. Tetrahedron 38: 871-909
104. Weinkam RJ, Jorgensen EC (1971) Free radical analogs of histidine. J Am Chem Soc 93: 7028-7033
105. Weitz IS, Pellegrini M, Mierke DF, Chorev M (1997) Synthesis of a trisubstituted 1,4-diazepine-3-one-based dipeptidomimetic as a novel molecular scaffold. J Org Chem 62: 2527-2534
106. Werner RM, Shokek O, Davis JT (1997) Preparation of 4-oxo-L-norvaline via diazomethane homologation of β-aspartyl semialdehyde. J Org Chem 62: 8243-8246
107. Wernic D, DiMaio J, Adams J (1989) Enantiospecific synthesis of L-α-aminosuberic acid. Synthetic applications in preparation of atrial natriuretic factor analogues. J Org Chem 54: 4224-4228
108. Weygand F, Fritz H (1965) Über N-TFA-Asparaginsäure-Derivate. Chem Ber 98: 72-82
109. Williams RM (1989) Synthesis of optically active α-amino acids. Pergamon Press, Oxford
110. Williams RM, Liu J (1998) Asymmetric synthesis of differentially protected 2,7-diaminosuberic acid, a ring closure methatesis approach. J Org Chem 63: 2130-2132
111. Winkler D, Burger K (1996) Synthesis of enantiomerically pure D- and L-Armentomycin and its difluoro analogues from aspartic acid. Synthesis: 1419-1421