Document Detail


Synthesis of stereospecifically deuterated phenylalamines and determination of their configuration.
MedLine Citation:
PMID:  13996     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
1. Starting from trans-cinnamic acid a chiral (-)3-phenyl-[2,3-2H]propionic acid has been synthesized using Clostridium kiuyveri cells as catalyst. 2. The chiral dideuterated acid has been converted by chemical methods to a mixture of (2R) and (2S)-phenyl[2,3-2H]-alanine. 3. By means of 1H nuclear magnetic resonance spectroscopy and the action of D and L-amino acid oxidase the configuration of the phenylalamine has been shown to be (2R, 3S) and (2S, 3S), respectively. The labelled phenylalanine is thus sterically and isotopically homogenous at position 3 but heterogenous at position 2.
Authors:
K Bartl; C Cavalar; T Krebs; E Ripp; J Rétey; W E Hull; H Günther; H Simon
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  European journal of biochemistry / FEBS     Volume:  72     ISSN:  0014-2956     ISO Abbreviation:  Eur. J. Biochem.     Publication Date:  1977 Jan 
Date Detail:
Created Date:  1977-04-30     Completed Date:  1977-04-30     Revised Date:  2007-07-23    
Medline Journal Info:
Nlm Unique ID:  0107600     Medline TA:  Eur J Biochem     Country:  GERMANY, WEST    
Other Details:
Languages:  eng     Pagination:  247-50     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Amino Acid Oxidoreductases / metabolism
Cinnamates
D-Amino-Acid Oxidase / metabolism
Deuterium*
Fourier Analysis
Isotope Labeling*
Magnetic Resonance Spectroscopy
Molecular Conformation
Phenylalanine* / chemical synthesis
Propionates
Stereoisomerism
Chemical
Reg. No./Substance:
0/Cinnamates; 0/Propionates; 63-91-2/Phenylalanine; 7782-39-0/Deuterium; EC 1.4.-/Amino Acid Oxidoreductases; EC 1.4.3.3/D-Amino-Acid Oxidase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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