System and method for solution phase gap peptide synthesis
AssigneeTexas Tech University System
InventorsGuigen Li, Cole Seifert
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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.
Claims9
A method of attaching a protecting group to an amino acid, wherein the method comprises:
- reacting a protecting group selected from the group consisting of:
- wherein:
- R is selected from the group consisting of:
- H, Me, and OMe;
- Y is selected from the group consisting of S and NH in 1B, or
- Y is selected from the group consisting of:
- O, S, and NH in 1C, 1D and 1E;
- and
- X is selected from the group consisting of:
- O, S, and NH
- with the amino acid to form:
- wherein Pg is a protecting group and Z is a general variable.
A method of performing a Group Assisted Purification (GAP) peptide synthesis, wherein the method comprises the steps of attaching a protecting group to an amino acid followed by Fmoc-tBu-based solution phase peptide synthesis (SolPPS) coupling reactions on the resulting amino acid having the attached protecting group, wherein the protecting group is selected from the group consisting of:
- wherein:
- R is selected from the group consisting of:
- H, Me, and OMe;
- Y is selected from the group consisting of:
- S and NH for 1B;
- or
- Y is selected from the group consisting of:
- O, S, and NH for 1C, 1D and 1E, and
- X is selected from the group consisting of:
- O, S, and NH.
Dependencies are inferred from the claim text.