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 › peer-review

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

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 %).",

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author = "Seifert, {Cole W.} and Armando Paniagua and White, {Gabrielle A.} and Lucy Cai and Guigen Li",

note = "Publisher Copyright: Copyright {\textcopyright} 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

year = "2016",

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doi = "10.1002/ejoc.201600026",

language = "English",

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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 › peer-review

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T2 - An Fmoc/tBu Synthesis of Thymopentin Free from Polymers, Chromatography and Recrystallization

AU - Seifert, Cole W.

AU - Paniagua, Armando

AU - White, Gabrielle A.

AU - Cai, Lucy

AU - Li, Guigen

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KW - Amino acids

KW - GAP chemistry

KW - Peptides

KW - Protecting groups

KW - Synthetic methods

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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

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