Synthesis strategy for gap protecting group
AssigneeSederma
InventorCole Seifert
Life of this patent
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Abstract
The present invention relates to a novel synthesis method to form particular molecules. These molecules have multiple uses, most notably in the field of protecting groups used throughout organic and synthetic chemistry. The disclosed method is safer, more cost- and time-effective, and more amenable to large scale production than those currently known in the art. The protecting groups synthesized are useful in GAP peptide synthesis.
Claims12
A protecting group for chemical synthesis, selected from the group consisting of:
- wherein:
- in (1E):
- Y is selected from the group consisting of:
- —S— and —NH—;
- R′ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- R″ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3- ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- in (1F):
- Y is selected from the group consisting of:
- —O—, —S—, and —NH—;
- Z is selected from the group consisting of:
- —O—, —S—, —NMe, and —NH—;
- R′ is selected from the group consisting of:
- -Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- R″ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20.
A method comprising the step of synthesizing a protecting group, wherein the protecting group is selected from a group consisting of:
- wherein:
- in (1B):
- R is selected from the group consisting of:
- —H, -Me, and —OMe;
- Y is selected from the group consisting of:
- —S— and —NH—;
- R′ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- R″ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- in (1E):
- Y is selected from the group consisting of:
- —S— and —NH—;
- R′ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- R″ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- in (1C) and (1F):
- R is selected from the group consisting of:
- —H, -Me, and —OMe;
- Y is selected from the group consisting of:
- —O—, —S—, and —NH—;
- Z is selected from the group consisting of:
- —O—, —S—, —NMe, and —NH—;
- R′ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- R″ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20.
A method of performing Group Assisted Purification (GAP) peptide synthesis, wherein the method comprises the steps of attaching a protecting group to an amino acid via a nucleophilic moiety followed by Fmoc-tBu-based solution phase peptide synthesis (SoIPPS) coupling reactions on the resulting amino acid having the attached protecting group;
- wherein the protecting group comprises at least one of:
- wherein:
- in (1B):
- R is selected from the group consisting of:
- —H, -Me, and —OMe;
- Y is selected from the group consisting of:
- —S— and —NH—;
- R′ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- R″ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- in (1E):
- Y is selected from the group consisting of:
- —S—, and —NH—;
- R′ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- R″ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- in (1C) and (1F):
- R is selected from the group consisting of:
- —H, -Me, and —OMe;
- Y is selected from the group consisting of:
- —O—, —S—, and —NH—;
- Z is selected from the group consisting of:
- —O—, —S—, —NMe, and —NH—;
- R′ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20;
- and
- R″ is selected from the group consisting of:
- Me, iPr, tBu, Ph, 2-ClPh, 4-ClPh, 3-ClPh, 3,5-Cl2Ph, and —(CH2)n-CH3 where n=any integer >0 and <20.
Dependencies are inferred from the claim text.