Document Detail

Coulombic effects on the traceless Staudinger ligation in water.
MedLine Citation:
PMID:  18314338     Owner:  NLM     Status:  MEDLINE    
The traceless Staudinger ligation can be mediated by phosphinothiols under physiological conditions. Proximal positive charges are necessary to achieve that transformation, presumably because those charges discourage protonation of the key iminophosphorane intermediate. Here, a series of cationic phosphinothiols is used to probe Coulombic effects on the traceless Staudinger ligation in aqueous buffers. The reagent bis(m-N,N-dimethylaminomethylphenyl)phosphinomethanethiol (3) is found to be superior to others, both in its ability to mediate the traceless Staudinger ligation in water and in the efficiency of its synthesis.
Annie Tam; Ronald T Raines
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2008-02-16
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  17     ISSN:  1464-3391     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2009 Feb 
Date Detail:
Created Date:  2009-02-03     Completed Date:  2009-04-15     Revised Date:  2014-09-16    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  1055-63     Citation Subset:  IM    
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MeSH Terms
Magnetic Resonance Spectroscopy
Organothiophosphorus Compounds / chemical synthesis,  chemistry*
Peptides / chemical synthesis,  chemistry
Phenylenediamines / chemical synthesis,  chemistry*
Sulfhydryl Compounds / chemical synthesis,  chemistry*
Water / chemistry*
Grant Support
Reg. No./Substance:
0/Organothiophosphorus Compounds; 0/Peptides; 0/Phenylenediamines; 0/Sulfhydryl Compounds; 0/bis(m-N,N-dimethylaminomethylphenyl)phosphinomethanethiol; 059QF0KO0R/Water

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