Document Detail

Studies on peptides. LXXXI. Application of a new arginine derivative, NG-mesitylene-2-sulfonylarginine, to the synthesis of substance P and neurotensin.
MedLine Citation:
PMID:  489255     Owner:  NLM     Status:  MEDLINE    
A new devised arginine derivative, NG-mesitylene-2-sulfonylarginine, Arg(Mts), was employed for the synthesis of hypothalamic substance P and neurotensin. The former was obtained in 74% yield by treatment of the protected undecapeptide amide, Z - Arg(Mts) - Pro - Lys(Z) - Pro - Gln - Gln - Phe - Phe - Gly - Leu - Met(O)-NH2, with methanesulfonic acid in the presence of anisole followed by reduction of the sulfoxide with 2-mercaptoethanol. The latter was obtained in 54% yield by the similar treatment of the protected tridecapeptide ester, Z - Pyr - Leu - Tyr - Glu(OBzl) - Asn - Lys(Z) - Pro - Arg(Mts) - Arg(Mts) - Pro - Tyr - Ile - Leu - OBzl, with methanesulfonic acid. As scavenger, a mixture of anisole-thioanisole-o-cresol (1:1:1, by vol.) was employed to suppress the side reaction, O-mesitylene-2-sulfonation of the Tyr residue.
H Yajima; K Akaji; K Mitani; N Fujii; S Funakoshi; H Adachi; M Oishi; Y Akazawa
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  International journal of peptide and protein research     Volume:  14     ISSN:  0367-8377     ISO Abbreviation:  Int. J. Pept. Protein Res.     Publication Date:  1979 Aug 
Date Detail:
Created Date:  1979-12-20     Completed Date:  1979-12-20     Revised Date:  2003-11-14    
Medline Journal Info:
Nlm Unique ID:  0330420     Medline TA:  Int J Pept Protein Res     Country:  DENMARK    
Other Details:
Languages:  eng     Pagination:  169-76     Citation Subset:  IM    
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MeSH Terms
Amino Acid Sequence
Arginine / analogs & derivatives*
Muscle Contraction / drug effects
Muscle, Smooth / drug effects
Neurotensin / chemical synthesis*,  pharmacology
Peptide Fragments
Substance P / chemical synthesis*,  pharmacology
Reg. No./Substance:
0/Peptide Fragments; 33507-63-0/Substance P; 39379-15-2/Neurotensin; 74-79-3/Arginine

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

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