Document Detail


Solution-phase and solid-phase syntheses of enzyme inhibitor RK-682 and antibiotic agglomerins.
MedLine Citation:
PMID:  16018718     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The enzyme inhibitor RK-682 (5R)-(+)-1 was prepared in solution and on a solid support from (2R)-glycerates in five steps and ca. 40% overall yield. Key steps were a ring-closing tandem addition-Wittig alkenation reaction of the respective protected or immobilized glycerates with the ylide Ph(3)PCCO and the 3-acylation of the tetronic acids thus obtained with palmitic acid. A similar route extended by a mesylation-elimination sequence led to antibiotic agglomerins A-C 2 featuring 3-acyl-5-methylidenetetronic acid structures.
Authors:
Rainer Schobert; Carsten Jagusch
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  70     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2005 Jul 
Date Detail:
Created Date:  2005-07-15     Completed Date:  2005-09-12     Revised Date:  2007-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6129-32     Citation Subset:  IM    
Affiliation:
Organisch-Chemisches Laboratorium, Universität Bayreuth, 95440 Bayreuth, Germany. rainer.schobert@uni-bayreuth.de
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MeSH Terms
Descriptor/Qualifier:
4-Butyrolactone / analogs & derivatives
Acylation
Anti-Bacterial Agents / chemical synthesis*
Enzyme Inhibitors / chemical synthesis*
Furans / chemistry
Glyceric Acids / chemistry
Molecular Structure
Palmitic Acid / chemistry
Phosphoprotein Phosphatases / antagonists & inhibitors*,  chemical synthesis
Chemical
Reg. No./Substance:
0/Anti-Bacterial Agents; 0/Enzyme Inhibitors; 0/Furans; 0/Glyceric Acids; 0/RK 682; 125620-70-4/agglomerin A; 125620-71-5/agglomerin B; 125620-72-6/agglomerin C; 473-81-4/glyceric acid; 4971-56-6/tetronic acid; 57-10-3/Palmitic Acid; 96-48-0/4-Butyrolactone; EC 3.1.3.16/Phosphoprotein Phosphatases

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


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