Synthesis of (2S,3R)-3-amino-2-hydroxydecanoic acid and its enantiomer: a non-proteinogenic amino acid segment of the linear pentapeptide microginin

A directed manipulation of the functional groups at C3 and C4 of D-glucose was demonstrated to synthesize naturally occurring (2S,3R)-α-hydroxy-β-aminodecanoic acid (AHDA, 2a) and its enantiomer 2b. The enantiomer of 2a is the N-terminal part of the natural linear pentapeptide microginin, which is u...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2014-03, Vol.10 (1), p.667-671
Main Authors: Rohokale, Rajendra S, Dhavale, Dilip D
Format: Article
Language:English
Subjects:
AHDA
carbohydrate
Chemistry
chiron approach
enantioselective
Full Research Paper
natural products
non-proteinogenic amino acid
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Summary:A directed manipulation of the functional groups at C3 and C4 of D-glucose was demonstrated to synthesize naturally occurring (2S,3R)-α-hydroxy-β-aminodecanoic acid (AHDA, 2a) and its enantiomer 2b. The enantiomer of 2a is the N-terminal part of the natural linear pentapeptide microginin, which is used as an antihypertensive agent.
ISSN:1860-5397
1860-5397
DOI:10.3762/bjoc.10.59