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    
Abstract/OtherAbstract:
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.
Authors:
H Yajima; K Akaji; K Mitani; N Fujii; S Funakoshi; H Adachi; M Oishi; Y Akazawa
Related Documents :
11522835 - Five-base codons for incorporation of nonnatural amino acids into proteins.
17690425 - Photoreactivity of amino acids: tryptophan-induced photochemical events via reactive ox...
17432905 - Synthesis of biologically active peptide nucleic acid-peptide conjugates by sortase-med...
16231205 - Catalytically increased prebiotic peptide formation: ditryptophan, dilysine, and diserine.
19432465 - Pd(o2ccf3)2/benzoquinone: a versatile catalyst system for the decarboxylative olefinati...
18488885 - Hyaluronic acid gel fillers in the management of facial aging.
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    
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms
Descriptor/Qualifier:
Amino Acid Sequence
Animals
Arginine / analogs & derivatives*
Muscle Contraction / drug effects
Muscle, Smooth / drug effects
Neurotensin / chemical synthesis*,  pharmacology
Peptide Fragments
Rabbits
Substance P / chemical synthesis*,  pharmacology
Chemical
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


Previous Document:  Electron microscope study on human ceruloplasmin.
Next Document:  Empirical torsional potential functions from protein structure data. Phi- and psi-potentials for non...