| Solution-phase and solid-phase syntheses of enzyme inhibitor RK-682 and antibiotic agglomerins. | |
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MedLine Citation:
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PMID: 16018718 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Rainer Schobert; Carsten Jagusch |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 70 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2005 Jul |
Date Detail:
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Created Date: 2005-07-15 Completed Date: 2005-09-12 Revised Date: 2007-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 6129-32 Citation Subset: IM |
Affiliation:
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Organisch-Chemisches Laboratorium, Universität Bayreuth, 95440 Bayreuth, Germany. rainer.schobert@uni-bayreuth.de |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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4-Butyrolactone
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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:
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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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