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By John S. Davies

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Extra info for Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 35)

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5, 5Diaryl-2-amino-4-pentenoates (74) have been made402 using Oppolzer’s sultam and a Pd-catalysed stereoselective hydrostannylation. L-2-Amino-3-(6, 7-dimethoxy-4-coumaryl) propionic acid, a fluorescent molecule, has been synthesized,403 and an analogue, L-2-amino-3-(7-methoxy-4-coumaryl) propionic acid,404 also a fluorogen, has been made from an oxazinone alkylated with the fluorogenic group. A novel fluorescent amino acid has been synthesised405 in the form of N-Boc-3-[2-(1H-indol-3-yl)benzoxazol-5-yl]-L-alanyl methyl ester from 3-nitro-L-tyrosine and 1H-indole-3-carboxaldehyde.

Included is a wider study395 of the application of aza Diels-Alder reactions was a protocol to make anthracenylglycine derivatives. A range of heterocyclic amino acid systems396 including quinoxalines, pyrazines and 1, 2, 4-triazines have been obtained from the reaction of diamines and amidrazones with a-amino acid vicinal tricarbonyls. N-(Iodoethyl)- and N-(3-iodopropyl)pyrimidines and purines have shown397 to undergo conjugate radical addition to chiral oxazolidinone acceptors to give purine and pyrimidine amino acids.

A first asymmetric synthesis134 has been recorded for (2S)- and (2R)-amino-3,3-dimethoxy propanoic acid through quenching of a chiral glycine titanium enolate with trimethyl orthoformate, and (S)-a-aminooleic acid has been formed135 from Me (2S)-2-[bis-(Boc)amino]-5-oxopentanoate. 13 Amino Acids, Pept. 3 Synthesis of a-Alky1 a-Amino Acids. – The chromatographically isolatable diastereoisomers of 2, 2-disubstituted 2H-azirin-3-amine (29) provided136 useful synthons for the synthesis of (R)- and (S)-isomers of isovaline, 2methylvaline, 2-cyclopentylalanine, 2-methylleucine and 2-methylphenylalanine, and in an extension of the work137 2-methyltyrosine and 2-methylDOPA were produced.

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