(+)-Zwittermicin A: Assignment of its Complete Configuration by Total Synthesis of the Enantiomer and Implication of D-Serine in its Biosynthesis

D‐Serine is the prime suspect: The total synthesis of (−)‐zwittermicin A has been achieved from a suitably protected C2‐symmetric diamino tetraol unit and has allowed the complete stereochemical assignment of natural (+)‐zwittermicin A. The unexpected 14R configuration implies the involvement of a “...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-01, Vol.47 (42), p.8086-8089
Main Authors: Rogers, Evan W, Dalisay, Doralyn S, Molinski, Tadeusz F
Format: Article
Language:English
Subjects:
amino alcohols
Biological Products - pharmacology
Candida - drug effects
Candida - pathogenicity
configuration determination
Magnetic Resonance Spectroscopy
Molecular Conformation
natural products
Peptides - chemical synthesis
Peptides - chemistry
Peptides - metabolism
Peptides - pharmacology
polyketides
Serine - biosynthesis
Serine - chemistry
Stereoisomerism
total synthesis
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Summary:D‐Serine is the prime suspect: The total synthesis of (−)‐zwittermicin A has been achieved from a suitably protected C2‐symmetric diamino tetraol unit and has allowed the complete stereochemical assignment of natural (+)‐zwittermicin A. The unexpected 14R configuration implies the involvement of a “D‐serine” motif in the biosynthesis of (+)‐zwittermicin A (see scheme).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200801561