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Soluble Peptidyl Phosphoranes for Metal-Free, Stereoselective Ligations in Organic and Aqueous Solution.
MedLine Citation:
PMID:  22136619     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
Protocols for solid-phase syntheses of soluble peptidyl phosphoranes are presented. Various supported phosphoranylidene acetates were prepared on Rink amide or via alkylation of trialkyl- and triarylphosphines with bromoacetyl Wang ester. C-Acylation was conducted racemization-free with activated Fmoc-amino acids, followed by SPPS (solid-phase peptide synthesis). Acidic conditions released decarboxylated peptidyl phosphoranes into solution. The protocol allowed for the electronic variation of peptidyl phosphoranes which were investigated in ligation reactions with azides in organic and aqueous solvents.
Authors:
Ahsanullah; Samer I Al-Gharabli; Jörg Rademann
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2011-12-2
Journal Detail:
Title:  Organic letters     Volume:  -     ISSN:  1523-7052     ISO Abbreviation:  -     Publication Date:  2011 Dec 
Date Detail:
Created Date:  2011-12-5     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
Affiliation:
Institute of Pharmacy, University of Leipzig , Brüderstrasse 34, 04103 Leipzig, Germany, Leibniz Institute of Molecular Pharmacology (FMP), Robert-Rössle-Strasse 10, 13125 Berlin, Germany, and Chemical-Pharmaceutical Engineering, German-Jordanian University , 35247 Amman, Jordan.
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