Synthesis of nonracemic hydroxyglutamic acids

Glutamic acid is involved in several cellular processes though its role as the neurotransmitter is best recognized. For detailed studies of interactions with receptors a number of structural analogues of glutamic acid are required to map their active sides. This review article summarizes syntheses o...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2019-01, Vol.15 (1), p.236-255
Main Authors: Piotrowska, Dorota G, Głowacka, Iwona E, Wróblewski, Andrzej E, Lubowiecka, Liwia
Format: Article
Language:English
Subjects:
amino acids
asymmetric synthesis
Biological activity
Carbon
Chemistry
chiral catalysis
chiral pool
glutamate analogues
Glutamic acid
Hydrogen bonding
Hydrogen bonds
Hydroxyproline
Ligands
Natural products
Proline
Protected derivatives
Review
Serine
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Summary:Glutamic acid is involved in several cellular processes though its role as the neurotransmitter is best recognized. For detailed studies of interactions with receptors a number of structural analogues of glutamic acid are required to map their active sides. This review article summarizes syntheses of nonracemic hydroxyglutamic acid analogues equipped with functional groups capable for the formation of additional hydrogen bonds, both as donors and acceptors. The majority of synthetic strategies starts from natural products and relies on application of chirons having the required configuration at the carbon atom bonded to nitrogen (e.g., serine, glutamic and pyroglutamic acids, proline and 4-hydroxyproline). Since various hydroxyglutamic acids were identified as components of complex natural products, syntheses of orthogonally protected derivatives of hydroxyglutamic acids are also covered.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.15.22