Publication Date:
1993-01-22
Description:
Organic reactions are often limited by stereoelectronic constrains that appear along the reaction coordinate. An antibody has been generated that overcomes these constraints and catalyzes a highly disfavored chemical transformation. The antibody facilitates the difficult 6-endo-tet ring closure of an epoxy-alcohol to form a tetrahydropyran. The catalyzed process is in formal violation of what has become known as Baldwin's rules for ring-closure reactions. In addition to controlling the regiochemistry of the disfavored cyclization reaction, these catalytic antibodies resolve enantiomeric substrates to afford a stereochemically pure product. The principles demonstrated in this study may be applicable to other disfavored chemical processes.〈br /〉〈span class="detail_caption"〉Notes: 〈/span〉Janda, K D -- Shevlin, C G -- Lerner, R A -- New York, N.Y. -- Science. 1993 Jan 22;259(5094):490-3.〈br /〉〈span class="detail_caption"〉Author address: 〈/span〉Department of Molecular Biology, Scripps Research Institute, La Jolla, CA 92037.〈br /〉〈span class="detail_caption"〉Record origin:〈/span〉 〈a href="http://www.ncbi.nlm.nih.gov/pubmed/8424171" target="_blank"〉PubMed〈/a〉
Keywords:
Antibodies/*metabolism
;
Catalysis
;
Enzymes/metabolism
;
Heterocyclic Compounds/*chemistry
;
Indicators and Reagents
;
Isomerism
;
Kinetics
Print ISSN:
0036-8075
Electronic ISSN:
1095-9203
Topics:
Biology
,
Chemistry and Pharmacology
,
Computer Science
,
Medicine
,
Natural Sciences in General
,
Physics
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