Solid-Phase Synthesis of Aromatic-Ring Peptide Derivatives
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Solution Overview
Problem
Existing liquid phase synthesis methods for compounds with an aromatic 6-membered ring, such as thiopeptides, are inefficient for producing a wide variety of derivatives due to the need for individual preparation of peptide sequences and complex purification processes.
Innovation Solution
A solid-phase synthesis method involving reacting an amino acid or peptide bonded to a solid-phase carrier with a specific compound to form a peptide including an aromatic 6-membered ring, followed by deprotection, amino acid condensation, and cyclization reactions.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Adaptability or versatility
If liquid phase synthesis method is used for thiopeptides, then synthesis of specific compound is achieved, but synthesis of wide variety of derivatives is difficult and purification is complicated
Solution Approach 1:
The patent introduces a solid-phase carrier as an intermediary support for peptide synthesis. The peptide sequence is synthesized while attached to the solid-phase carrier, which acts as a mediator that simplifies purification by allowing easy separation of the synthesized peptide from reaction byproducts through filtration, thereby enabling versatile synthesis of multiple derivatives without complicated purification operations for each compound
2Productivity
If liquid phase synthesis method is used, then specific peptide sequence is synthesized, but individual preparation for each target peptide is required
Solution Approach 1:
The patent applies universality by using a standardized solid-phase synthesis platform that can synthesize multiple different peptide sequences using the same basic methodology and reagents. By attaching different amino acid sequences to the same type of solid-phase carrier and using universal coupling reagents, the system enables efficient production of various thiopeptide derivatives without requiring individual preparation procedures for each target peptide
3Manufacturing precision
If liquid phase synthesis is used, then synthesis reaction is performed, but complicated purification operation is required to remove impurities
Solution Approach 1:
The solid-phase carrier serves as an intermediary that facilitates simplified purification. After synthesis on the solid-phase carrier, the peptide can be cleaved from the carrier and purified by simple filtration and washing steps, which effectively remove impurities without requiring complicated purification operations, thus achieving high purity with ease of operation
Data Source
Figure 1a~1c
Figure 2a~2c
Figure 3
AI summary
The present invention provides a method which makes it possible to simply produce a peptide including an aromatic 6-membered ring in the backbone. The present invention relates to a production method for a compound represented by Formula (I), the method including reacting an amino acid or amino acid derivative, or a peptide, which is bonded to a solid-phase carrier and has a free amino group, or a solid-phase carrier having a free amino group with a compound represented by Formula (1) to obtain a compound represented by Formula (2), in which a compound obtained by deprotecting PG of the compound represented by Formula (2) is optionally subjected to one or more amino acid condensation reactions and then is cleaved from the solid-phase carrier to perform a cyclization reaction.