GAP Peptide Synthesis through the Design of a GAP Protecting Group: An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization

Cole W. Seifert; Armando Paniagua; Gabrielle A. White; Lucy Cai; Guigen Li

doi:10.1002/ejoc.201600026

GAP Peptide Synthesis through the Design of a GAP Protecting Group: An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization

Cole W. Seifert, Armando Paniagua, Gabrielle A. White, Lucy Cai, Guigen Li

Chemistry and Biochemistry

Research output: Contribution to journal › Article

20 Scopus citations

Abstract

A novel method for Fmoc/tBu 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 %). Fmoc/tBu solution-phase peptide synthesis and the development of a new benzyl-type group-assisted purification (GAP) protecting group is reported. This new GAP protecting group replaces a polymer support, facilitating C→N Fmoc peptide synthesis without chromatography or recrystallization. Over 1 gram of the immunostimulant, thymopentin, was synthesized in high overall yield (83 %) and purity (99 %).

Original language	English
Pages (from-to)	1714-1719
Number of pages	6
Journal	European Journal of Organic Chemistry
Volume	2016
Issue number	9
DOIs	https://doi.org/10.1002/ejoc.201600026
State	Published - Mar 1 2016

Keywords

Amino acids
GAP chemistry
Peptides
Protecting groups
Synthetic methods

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10.1002/ejoc.201600026

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Seifert, C. W., Paniagua, A., White, G. A., Cai, L., & Li, G. (2016). GAP Peptide Synthesis through the Design of a GAP Protecting Group: An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization. European Journal of Organic Chemistry, 2016(9), 1714-1719. https://doi.org/10.1002/ejoc.201600026

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GAP Peptide Synthesis through the Design of a GAP Protecting Group : An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization. / Seifert, Cole W.; Paniagua, Armando; White, Gabrielle A.; Cai, Lucy; Li, Guigen.

In: European Journal of Organic Chemistry, Vol. 2016, No. 9, 01.03.2016, p. 1714-1719.

Research output: Contribution to journal › Article

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