Synthetic method of apraglutide
By replacing some amino acids with pseudo-pro dipeptide and using a holistic coupling method with DIC/HOBt condensing agent, the problems of low purity and yield caused by hydrophobic amino acid aggregation in the synthesis of apalugglutide were solved, achieving a high-purity and high-yield synthesis suitable for industrial production.
CN120623311APending Publication Date: 2025-09-12SINOPEP ALLSINO BIOPHARMACEUTICAL CO LTD +1
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Patent Information
- Application Number
- CN202411849999.7
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-12-16
- Publication Date
- 2025-09-12
AI Technical Summary
Technical Problem
The synthesis method of apalutamide in the prior art has a folding problem caused by the aggregation of hydrophobic amino acids, resulting in incomplete coupling, low purity and yield, and difficulty in achieving industrial production.
Method used
Pseudopro dipeptide was used to replace some amino acids, and DIC/HOBt was used as a condensation agent to synthesize apalutamide by overall coupling of tripeptide fragments. The specific steps included stepwise coupling and cleavage processes.
Benefits of technology
The purity and yield of apalutamide are improved, the operation process is simplified, and it is conducive to industrial production.
✦ Generated by Eureka AI based on patent content.
Abstract
The invention provides a solid-phase synthesis method of apraglutide, and belongs to the field of medicinal chemistry. The method comprises the following steps: according to an amino acid sequence from an N end to a C end of a peptide chain of the apraglutide, adopting a pseudo-prole dipeptide Phe-Ser [PSI (Me, Me) Pro] for Phe-Ser (tBu) at No. 6 to No. 7 sites in the sequence, adopting a pseudo-prole dipeptide Gln (Trt)-Thr (tBu) at No. 28 to No. 29 sites as a pseudo-prole dipeptide Gln (Trt)-Thr [PSI (Me, Me) Pro], and taking Glu (OtBu)-NIE-D-Phe at No. 9 to No. 11 sites as a whole of a tripeptide fragment for coupling to obtain the apraglutide. The solid-phase synthesis method of the apraglutide, provided by the invention, has the advantages of low cost, simplicity in operation, high yield and high purity, and solves the problems that in the prior art, hydrophobic amino acid aggregation causes difficult sequence aggregation, folding is caused, connection is difficult, the yield is seriously influenced by excessive deletion, and industrial production is not facilitated.
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