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GAP Peptide Synthesis through the Design of a GAP Protecting Group: An Fmoc/ t Bu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization
Author(s) -
Seifert Cole W.,
Paniagua Armando,
White Gabrielle A.,
Cai Lucy,
Li Guigen
Publication year - 2016
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201600026
Subject(s) - chemistry , protecting group , recrystallization (geology) , peptide synthesis , thymopentin , peptide , solid phase synthesis , yield (engineering) , combinatorial chemistry , chromatography , organic chemistry , alkyl , biochemistry , paleontology , materials science , metallurgy , immunology , biology
A novel method for Fmoc/ t Bu solution‐phase peptide synthesis and the development of a new benzyl‐type group‐assisted purification (GAP) protecting group is reported. This GAP protecting group is utilized in place of a polymer support, facilitating C→N Fmoc peptide synthesis without chromatography or recrystallization. The GAP group can be added and removed in high yield, and was used to synthesize over 1 gram of the immunostimulant, thymopentin, in high overall yield (83 %) and purity (99 %).