Stereoselective Syntheses of (E)-α,β-Didehydroamino Acid and Peptide Containing Its Residue Utilizing Oxazolidinone Derivative | Zendy

Miki Kometani | Zendy; Kohki Ihara | Zendy; Rumi Kimura | Zendy; Hideki Kinoshita | Zendy

Open Access

Stereoselective Syntheses of (E)-α,β-Didehydroamino Acid and Peptide Containing Its Residue Utilizing Oxazolidinone Derivative

Author(s) -

Miki Kometani,

Kohki Ihara,

Rumi Kimura,

Hideki Kinoshita

Publication year - 2009

Publication title -

bulletin of the chemical society of japan

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.145

H-Index - 99

eISSN - 1348-0634

pISSN - 0009-2673

DOI - 10.1246/bcsj.82.364

Subject(s) - chemistry , dipeptide , stereoselectivity , residue (chemistry) , selectivity , peptide , stereochemistry , derivative (finance) , coupling reaction , amino acid , base (topology) , combinatorial chemistry , organic chemistry , catalysis , biochemistry , financial economics , economics , mathematical analysis , mathematics

Reaction of methyl N-Boc-N-phenoxycarbonylglycinate with various aldehydes afforded the corresponding cis-4,5-oxazolidinone derivatives, which were effectively converted to (E)-α,β-didehydroamino acids by means of a base. Furthermore, N-deprotection of the oxazolidinone derivatives and subsequent coupling reaction with Boc-amino acid furnished the corresponding dipeptides, which were transformed to dipeptide containing α,β-didehydroamino acid with high E selectivity

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