Document Detail

Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities.
MedLine Citation:
PMID:  24179673     Owner:  NLM     Status:  Publisher    
Cysteine plays a number of important functional and structural roles in Nature, often in the realm of catalysis. Herein, we present an example of a cysteine-catalyzed Rauhut-Currier reaction for a potentially biomimetic synthesis of Sch-642305 and related analogs. In this key step of the synthesis we discuss interesting new discoveries and the importance of substrate-catalyst recognition, as well as cysteine's structural features. Also, we investigate the activity of Sch-642305 and four analogs in HIV-infected T-cells.
Alpay Dermenci; Philipp S Selig; Robert A Domaoal; Krasimir A Spasov; Karen S Anderson; Scott J Miller
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Publication Detail:
Journal Detail:
Title:  Chemical science (Royal Society of Chemistry : 2010)     Volume:  2     ISSN:  2041-6520     ISO Abbreviation:  Chem Sci     Publication Date:  2011 Aug 
Date Detail:
Created Date:  2013-11-1     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101545951     Medline TA:  Chem Sci     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 -8107 (USA).
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