Document Detail

Protein modification by diazotized arsanilic acid: synthesis and characterization of the phenylthiohydantoin derivatives of azobenzene arsonate-coupled tyrosine, histidine, and lysine residues and their sequential allotment in labeled peptides.
MedLine Citation:
PMID:  2500873     Owner:  NLM     Status:  MEDLINE    
Analytical procedures are elaborated for the sequential allotment of azobenzene arsonate binding sites in proteins and peptides. The reaction of diazotized arsanilic acid with proteins leads to covalent modification of tyrosine, histidine and, in part, lysine residues. Synthetic peptides containing these amino acids were modified with diazotized arsanilic acid and subjected to N-terminal sequence analysis. The amino acid derivatives phenylthiohydantoin(Pth)-azobenzene-arsonate-tyrosine, Pth-azobenzene-arsonate-histidine, and alpha-Pth-epsilon-hydroxycaproic acid are recovered upon Edman degradation of selected peptides. Phenylthiohydantoins of modified and nonmodified amino acids are fully separated by reverse-phase HPLC on a Zorbax-PTH column. For identification purposes, phenylthiohydantoins of azobenzene arsonate-labeled amino acids have been synthetized. They are characterized with respect to spectral absorption characteristics and retention times on reverse-phase supports.
B Schwaller; H Sigrist
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Analytical biochemistry     Volume:  177     ISSN:  0003-2697     ISO Abbreviation:  Anal. Biochem.     Publication Date:  1989 Feb 
Date Detail:
Created Date:  1989-08-10     Completed Date:  1989-08-10     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0370535     Medline TA:  Anal Biochem     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  183-7     Citation Subset:  IM    
Institute of Biochemistry, University of Berne, Switzerland.
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MeSH Terms
Amino Acid Sequence*
Amino Acids / analysis*,  chemical synthesis
Azo Compounds*
Hexanoic Acids / analysis
Histidine / analogs & derivatives,  analysis
Hydantoins / analysis*
Lysine / analogs & derivatives,  analysis
Phenylthiohydantoin / analogs & derivatives,  analysis*,  chemical synthesis
Tyrosine / analogs & derivatives,  analysis
Reg. No./Substance:
0/Amino Acids; 0/Azo Compounds; 0/Hexanoic Acids; 0/Hydantoins; 0/Peptides; 1191-25-9/6-hydroxyhexanoic acid; 2010-15-3/Phenylthiohydantoin; 55520-40-6/Tyrosine; 56-87-1/Lysine; 71-00-1/Histidine; 7334-23-8/p-Azobenzenearsonate

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