Document Detail


Photolabile multi-detachable p-alkoxybenzyl alcohol resin supports for peptide fragment or semi-synthesis.
MedLine Citation:
PMID:  7216616     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Two photolabile multi-detachable alkoxybenzyl alcohol resins, 2-[4-(oxymethyl)phenoxy]propionyl-resin 4 and 4-[4-(oxymethyl)phenoxymethyl]-3-nitrobenzamidomethyl-resin 5 have been synthesized. Bpoc-peptide attached to resin 4 or 5 when treated with 50% trifluoroacetic acid provided the free, unprotected peptide, but on photolysis gave Bpoc-peptide p-hydroxybenzyl ester. Removal of the p-hydroxybenzyl ester in aqueous base or by oxidative work up gave a protected Bpoc-peptide suitable for fragment synthesis at its C-terminus. However, methylation of the ester to Bpoc-peptide p-methoxybenzyl ester followed by removal of the Bpoc-group gave a protected peptide p-methoxybenzyl ester suitable for fragment coupling at its N-terminus. The efficacies of these resins were evaluated in the syntheses of a model tetrapeptide and an octapeptide by using N alpha-Bpoc-, Fmoc- and Nps-amino acids. The use of 2-thiopyridine with pyridinium hydrochloride as a new and efficient thiolytic reagent for the deprotection of the Nps-group was studied.
Authors:
J P Tam; R D Dimarchi; R B Merrifield
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.; Research Support, U.S. Gov't, P.H.S.    
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:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  0330420     Medline TA:  Int J Pept Protein Res     Country:  DENMARK    
Other Details:
Languages:  eng     Pagination:  412-25     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Amino Acid Sequence
Amino Acids
Benzyl Alcohols / chemical synthesis*
Benzyl Compounds / chemical synthesis*
Peptide Fragments
Peptides
Photolysis
Resins, Plant / chemical synthesis*
Trifluoroacetic Acid
Grant Support
ID/Acronym/Agency:
AM 01260/AM/NIADDK NIH HHS
Chemical
Reg. No./Substance:
0/Amino Acids; 0/Benzyl Alcohols; 0/Benzyl Compounds; 0/Peptide Fragments; 0/Peptides; 0/Resins, Plant; 76-05-1/Trifluoroacetic Acid

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


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