Document Detail

Side reaction of S-to-N acetamidomethyl shift during disulfide bond formation by iodine oxidation of S-acetamidomethyl-cysteine in a glutamine-containing peptide.
MedLine Citation:
PMID:  8838414     Owner:  NLM     Status:  MEDLINE    
During the time course of disulfide bond formation by iodine oxidation (in a methanolic and hydrochloric acid solution) of a cysteinyl(S-acetamidomethyl)-glutaminyl tridecapeptide, we observed by ESI, FAB mass spectrometry (pseudo-molecular ion and ion-fragments) and 1H-NMR a side reaction due to a shift of the Acm leaving group from cysteine to the carboxamide side chain of glutamine. This type of Acm-shift at low level was described previously by L.W. Mendelson et al. (Int. J. Pept. Protein Res. 35:249-257) for an aspariginyl-cysteinyl(S-acetamidomethyl) peptide in an anhydrous hydrochloric solution. We report here the efficiency of glutamine as a scavenger to suppress the S-->N shift of the acetamidomethyl group during S-acetamidomethyl cleavage and sulfhydryl oxidation with iodine, as the folded tridecapeptide was obtained with the expected molecular weight.
H Lamthanh; H Virelizier; D Frayssinhes
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Peptide research     Volume:  8     ISSN:  1040-5704     ISO Abbreviation:  Pept. Res.     Publication Date:    1995 Nov-Dec
Date Detail:
Created Date:  1997-02-06     Completed Date:  1997-02-06     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8913494     Medline TA:  Pept Res     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  316-20     Citation Subset:  IM    
CEA/Saclay, Gif sur Yvette, France.
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MeSH Terms
Acetylcysteine / analogs & derivatives*,  chemistry
Amino Acid Sequence
Chromatography, High Pressure Liquid
Disulfides / chemistry*
Glutamine / chemistry*
Iodine / chemistry*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Molecular Sequence Data
Molecular Weight
Peptides / chemistry*
Reg. No./Substance:
0/Disulfides; 0/Peptides; 19647-70-2/(S-acetamidomethyl)cysteine; 56-85-9/Glutamine; 616-91-1/Acetylcysteine; 7553-56-2/Iodine

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

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