Document Detail


3-nitro-2-pyridinesulfenyl (Npys) group. A novel selective protecting group which can be activated for peptide bond formation.
MedLine Citation:
PMID:  7216615     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The novel 3-nitro-2-pyridinesulfenyl (Npys) group, which is useful for the protection and the activation of amino and hydroxyl groups for peptide synthesis, is reported. The Npys group is readily introduced by treatment of amino acids with 3-nitro-2-pyridinesulfenyl chloride. The Npys group is easily removed by treatment with very dilute HCl, e.g. 0.1-0.2 N HCl in dioxane, but is is resistant to trifluoroacetic acid and 88% formic acid. Npys is also selectively removed under neutral conditions using triphenylphosphine or 2-pyridinethiol 1-oxide without affecting benzyloxycarbonyl (Z), tert-butyloxycarbonyl (Boc), 2-(4-biphenylyl)propyl(2)oxycarbonyl (Bpoc), 9-fluorenylmethyloxycarbonyl (Fmoc), benzyl (Bzl) or tert-butyl (tBu) protecting groups. The N-Npys and O-Npys groups when activated in the presence of RCOOH by the addition of tertiary phosphine form peptide or ester bonds via oxidation-reduction condensation. The important features of the Npys group are demonstrated through the synthesis of peptides in solution and by solid phase methodology without a formal deprotection procedure. In solid phase synthesis, 4-(Npys-oxymethyl) phenylacetic acid is used as the key intermediate for the introduction of the trifluoroacetic acid resistant 4-(oxymethyl) phenylacetamido linking group to the resin.
Authors:
R Matsueda; R Walter
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  International journal of peptide and protein research     Volume:  16     ISSN:  0367-8377     ISO Abbreviation:  Int. J. Pept. Protein Res.     Publication Date:  1980 Nov 
Date Detail:
Created Date:  1981-06-13     Completed Date:  1981-06-13     Revised Date:  2008-11-21    
Medline Journal Info:
Nlm Unique ID:  0330420     Medline TA:  Int J Pept Protein Res     Country:  DENMARK    
Other Details:
Languages:  eng     Pagination:  392-401     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Amino Acid Sequence
Amino Acids
Chemical Phenomena
Chemistry
Peptides
Pyridines / chemical synthesis*
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Peptides; 0/Pyridines; 77357-10-9/4-(3'-nitro-2'-pyridinesulfenyloxymethyl)phenylacetic acid

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


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