A concise, asymmetric synthesis of (2R,3R)-3-hydroxyaspartic acid.

Abstract:

:3-Hydroxyaspartic acid and its derivatives are found both in the free form and as peptide constituents in various microorganisms and fungi. Considering the biological importance of this amino acid and its potential utility as a multifunctional building block in organic syntheses, we have developed a short-step, asymmetric synthetic route to a strategically protected 3-hydroxyaspartic acid derivative in enantiopure form. The key steps in the synthesis involve, Sharpless asymmetric aminohydroxylation of commercially available trans-ethyl cinnamate, and, utilization of the phenyl group as a masked carboxylic acid synthon towards construction of the complete structural framework of the title compound.

journal_name

Amino Acids

journal_title

Amino acids

authors

Khalaf JK,Datta A

doi

10.1007/s00726-007-0595-z

subject

Has Abstract

pub_date

2008-08-01 00:00:00

pages

507-10

issue

2

eissn

0939-4451

issn

1438-2199

journal_volume

35

pub_type

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