Document Detail

Amino-acid conjugates of the hapten 2-phenyl-4-ethoxymethylene-5(4H)-oxazolone. Synthesis and confirmation of structure.
MedLine Citation:
PMID:  7775019     Owner:  NLM     Status:  MEDLINE    
2-Phenyl-4-ethoxymethylene-5(4H)-oxazolone (PhOx = CHOEt) was reacted with methylamine, and 2-phenyloxazole-4-carboxylic acid was coupled with methylamine. The spectroscopic properties of the two products were compared in order to confirm that aminolysis of PhOx = CHOEt occurs by displacement of the ethoxy group to give 2-phenyl-4-(substituted-methylene)-5(4H)-oxazolones and not by attack at the oxazolone-carbonyl followed by rearrangement to give 2-phenyloxazole-4-carboxamides. Ten crystalline conjugates were prepared and characterized by reacting PhOx = CHOEt with an excess of unprotected di- and trifunctional amino acid anions followed by purification by washing them with hydrochloric acid.
N L Benoiton; F Hudecz; F M Chen
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  International journal of peptide and protein research     Volume:  45     ISSN:  0367-8377     ISO Abbreviation:  Int. J. Pept. Protein Res.     Publication Date:  1995 Mar 
Date Detail:
Created Date:  1995-07-12     Completed Date:  1995-07-12     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0330420     Medline TA:  Int J Pept Protein Res     Country:  DENMARK    
Other Details:
Languages:  eng     Pagination:  266-71     Citation Subset:  IM    
Department of Biochemistry, University of Ottawa, Ontario, Canada.
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MeSH Terms
Amino Acids / chemistry*
Haptens / chemistry*
Magnetic Resonance Spectroscopy
Molecular Conformation
Oxazolone / analogs & derivatives*,  chemical synthesis,  chemistry
Peptides / chemical synthesis
Reg. No./Substance:
0/Amino Acids; 0/Haptens; 0/Peptides; 15646-46-5/Oxazolone

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