ISSN:
1573-3904
Keywords:
epimerization
;
phenol-based coupling reagent
;
solid phase peptide assembly
Source:
Springer Online Journal Archives 1860-2000
Topics:
Chemistry and Pharmacology
Notes:
Abstract In the course of comparing the effectiveness ofHATU, HBTU, and phenol-based coupling reagents, suchas the pentafluorophenyl, 2-nitrophenyl, and2,4,5-trichlorophenyl uronium salts by (a) formationof Fmoc-Ala-Val-OtBu, (b) (2+1) segment couplingand (c) stepwise solid phase peptide assembly oftypical model peptides such as the pentapeptideH-Tyr-Aib-Aib-Phe-Leu-NH2 and ACP decapeptide(65–74), we found a striking improvement of the lesseffective phenol-based coupling reagents (HPyOPfp,HPyONp, and HPyOTcp), both with regard to reactionrate and extent of epimerization, when HOAt was addedand a clear superiority of HAPyU (in the presence andabsence of HOAt) relative to the compounds derivedfrom HOBt, HOPfp, HONp, and HOTcp.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1023/A:1008967315605
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