System and method for solution phase gap peptide synthesis

Patent metadata

Field	Value
Publication number	US-12344632-B2
Application number	US-202117172732-A
Country	US
Kind code	B2
Filing date	Feb 10, 2021
Priority date	Dec 21, 2015
Publication date	Jul 1, 2025
Grant date	Jul 1, 2025

Abstract

Disclosed is a system and method for Fmoc/tBu solution-phase peptide synthesis including the development of a new benzyl-type GAP protecting group, and related uses thereto. This novel GAP protecting group is utilized in place of a polymer support, facilitating C to N Fmoc peptide synthesis without chromatography, recrystallization, or polymer supports. The GAP group can be added and removed in high yield.

First claim

What is claimed is:

1. A protecting group for Group Assisted Purification (GAP) peptide synthesis selected from the group consisting of:

wherein
wherein for 1B, 1C, and 1E, R is selected from the group consisting of: H, Me, and OMe;
wherein for 1D, R is selected from the group consisting of: H and 2, 3, or 4 OMe, except that R is not H in every position;
wherein for 1B and 1C, Y is selected from the group consisting of: O, S, and NH, except that for 1B when R=H, then Y is S; and
wherein for 1C, X is selected from the group consisting of: S and NH,
wherein for 1E, X is selected from the group consisting of: O, S, and NH, except that for 1E when R=H, X is not O.

Assignees

• Univ Texas Tech System

Inventors

• Li Guigen
• Seifert Cole

Classifications

• C07F9/5325

  Aromatic phosphine oxides or thioxides (P-C aromatic linkage) · CPC title

• C07F9/36

  Amides thereof · CPC title

• C07F9/3282 Primary

  Esters with hydroxyaryl compounds · CPC title

• C07K1/062 Primary

  for alpha- or omega-carboxy functions · CPC title

• C07K1/061 Primary

  using protecting groups · CPC title