Stereospecific synthesis of α-methylated amino acids

Amino Acids

Volumn 18, Issue 1, 2000, Pages 81-88

  Mzengeza, S ^a   Venkatachalam, T K ^a   Diksic, Mirko ^a  

^a MCGILL UNIVERSITY   (Canada)

Author keywords

2 tert butylimidazolidin 4 one; Amino acids; Stereospecific synthesis; methyl L phenylalanine; methyl L tryptophan

Indexed keywords

AMINO ACID; DIISOPROPYLAMINE; IMIDAZOLIDINE DERIVATIVE; INDOLE DERIVATIVE; LITHIUM DERIVATIVE; METHYL IODIDE; METHYLAMINE; N METHYLTRYPTOPHAN;

AMINO ACID SYNTHESIS; ARTICLE; ENANTIOMER; HYDROLYSIS; METHYLATION; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 0033952619     PISSN: 09394451     EISSN: None     Source Type: Journal    
DOI: 10.1007/s007260050007     Document Type: Article

References (19)

1. Crich D, Davies JW (1989) Asymmetric synthesis of a-alkylated tryptophan derivatives. J Chem Soc, Chem Commun: 1418-1418
2. 11C]methyl-L-tryptophan. Nucl Med Biol 23: 1005-1008
3. Diksic M (1991) Current aspects of the neurosciences, vol 3. In: Osborne NN (ed) MacMillan Press Ltd, London, pp 37-77
4. Gander-Coquoz M, Seebach D (1988) Herstellung entiomerenreiner, a-alkylierter Lysin-, Ornithin- and Tryptophan-Derivate. Helv Chim Acta 71: 224-236
5. 14C]methyl-L-tryptophan. Int J Appl Radiat Isot 44: 1167-1172
6. 11C]methyl-L-tryptophan for PET studies. Nucl Med Biol 22: 303-307
7. Naef R, Seebach D (1985) Herstellung enantiomerenreiner cis- oder trans-konfigurierter 2-(tert-Butyl)-3-methylimidazolidin-4-one aus den Aminosäuren (S)-Alanin, (S)-Phenylalanin, (R)-Phenylglycin, (S)-Methionin und (S)-Valin). Helv Chim Acta 68: 135-143
8. Paul PK, Sukumar M, Bardi R, Piazzesi AM, Valle G, Toniolo C, Balaram PJ (1986) Stereochemically constrained peptides. Theoretical and experimental studies on the conformations of peptides containing 1-aminocyclohexanecarboxylic acid. J Am Chem Soc 108: 6363-6370
9. 11C]tryptophan. Int J Appl Radiat Isot 45: 651-653
10. 14C-labelled a-methyl tyrosine. Int J Appl Radiat Isot 43: 979-987
11. Ramalingam K, Woodard RW (1985) A convenient synthesis of S-(5′-deoxy-5′-adenosyl)-(+)-2-methylhomocysteine. Tetrahedron Lett 26: 1135-1136
12. Saari WS, Freedman MB, Hartman RD, King SW, Raab AW, Randall WC, Engelhardt EL, Hirshmann R, Rosegay A, Ludden CT, Scriabine A (1978) Synthesis and antihypertensice activity of some ester progenitors of methyldopa. J Med Chem 21: 746-753
13. Saari WS, Halczenko W, Conchran DW, Dobrinska MR, Vincek WC, Titus DG, Gaul SL, Sweet CS (1984) 3-Hydroxy-·-methyltyrosine progenitors: synthesis and evaluation of some (2-oxo-1,3-dioxol-4-yl)methyl esters. J Med Chem 27: 713-717
14. Seebach D, Zimmermann J, Gysel U (1988) Totally stereoselective additions of 2,6-disubstituted 1,3-dioxin-4-ones (chiral acetoacetic acid derivatives). Synthetic and mechanistic aspects of remote stereoselectivity. J Am Chem Soc 110: 4763-4772
15. Schöllkopf U, Lonsky R, Lehr P (1985) Enantioselective synthesis of (R)-a-methyltryptophane methyl ester by the bislactim ether route. Liebigs Ann Chem 413-417
16. 3H]methyl-L-tryptophan. J Labelled Compd and Radiopharm 33: 1029-1038
17. Walsh JJ, Metzler DE, Powell D, Jacobson RA (1980) 2-(Hydoxymethyl)aspartic acid: synthesis, crystal structure, and reaction with a transaminase. J Am Chem Soc 102: 7136-7138
18. Williams RM (1989) Synthesis of optically active a-amino acids, vol 7. Pergamon Press, Oxford, pp 1-33
19. Williams RM, Myeong-Nyeo I (1991) Asymmetric synthesis of monosubstituted and a,a-disubstituted a-amino acids via diastereoselective gylcine enolate alkylations. J Am Chem Soc 113: 9276-9286