Polypeptide analogue as well as preparation method and application thereof

A technology for analogs and polypeptides, applied in the field of polypeptide analogs and their preparation, to achieve the effects of reducing muscle contraction, not easy to be oxidized, and good stability

Pending Publication Date: 2022-07-08
深圳深创生物药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

OA-GL12 has been reported in the literature to accelerate granulation tissue formation

Method used

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  • Polypeptide analogue as well as preparation method and application thereof
  • Polypeptide analogue as well as preparation method and application thereof
  • Polypeptide analogue as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Example 1: Preparation of Cyclic-GC12

[0049] Peptide sequence of Cyclic-GC12: CGLLSGINAEWPC (Disulfide cyclic peptide), molecular weight: 1360.57, and its structural formula is as follows:

[0050]

[0051] The preparation of Cyclic-GC12, the specific steps are as follows:

[0052] 1.1. Weigh 2.5 g (1 mmol) of H-Cys(Trt)-2-Chlorotryl Resin resin (Sub=0.40 mmol / g) into the reaction column, wash with DMF 3 times, and swell with DMF for 30 minutes. Weigh 2.6 g (6 mmol) of Fmoc-Pro-OH and 0.9 g (6.6 mmol) of HOBt, dissolve in DMF, add 1.2 g of DIC (9 mmol) in an ice-water bath at 0°C, activate for 5 minutes, add to the reaction column, and react for 2 hours. , the ninhydrin test result is negative (resin is colorless and transparent), then use DBLK (20% hexahydropyridine / DMF) to remove the Fmoc protecting group, then repeat the above operation, according to the sequence coupling Fmoc-Trp(Boc)- OH, Fmoc-Glu(OtBu)-OH, Fmoc-Ala-OH, Fmoc-Asn(Trt)-OH, Fmoc-Ile-OH, Fmoc-Gl...

Embodiment 2

[0054] Example 2: Preparation of Glyco-GC12

[0055] The peptide sequence of Glyco-GC12: GLLS(O-β-D-glucose) GINAEWPC, the molecular weight is: 1421.59, and its structural formula is as follows:

[0056]

[0057] The preparation of Glyco-GC12, the specific steps are as follows:

[0058] 2.1. Weigh 2.5 g (1 mmol) of H-Cys(Trt)-2-Chlorotrityl Resin resin (Sub=0.40 mmol / g) into the reaction column, wash with DMF 3 times, and swell with DMF for 30 minutes. Weigh 2.5 g (6 mmol) of Fmoc-Pro-OH and 0.9 g (6.6 mmol) of HOBt, dissolve them in DMF, add 1.2 g of DIC (9 mmol) in an ice-water bath at 0°C, activate for 5 minutes, add to the reaction column, and react for 2 hours. The Fmoc protecting group was then removed with DBLK. Repeat the above operation, according to the sequence coupling Fmoc-Trp(Boc)-OH, Fmoc-Glu(OtBu)-OH, Fmoc-Ala-OH, Fmoc-Asn(Trt)-OH, Fmoc-Ile-OH, Fmoc-Gly -OH, Fmoc-Ser(O-β-D-glucose)-OH, Fmoc-Leu-OH, Fmoc-Leu-OH, Boc-Gly-OH, washed with DMF, DCM, methanol i...

Embodiment 3

[0060] Example 3: Preparation of Pal-GC12

[0061] Peptide sequence of Pal-GC12: Pal-GLLSGINAEWPC, molecular weight: 1497.86, and its structural formula is as follows:

[0062]

[0063] The preparation of Pal-GC12, the specific steps are as follows:

[0064] 3.1. Weigh 2.5 g (1 mmol) of H-Cys(Trt)-2-Chlorotrityl Resin resin (Sub=0.40 mmol / g) into the reaction column, wash with DMF 3 times, and swell with DMF for 30 minutes. Weigh 2.5 g (6 mmol) of Fmoc-Pro-OH and 0.9 g (6.6 mmol) of HOBt, dissolve them in DMF, add 1.2 g of DIC (9 mmol) in an ice-water bath at 0°C, activate for 5 minutes, add to the reaction column, and react for 2 hours. The Fmoc protecting group was then removed with DBLK. Repeat the above operation, according to the sequence coupling Fmoc-Trp(Boc)-OH, Fmoc-Glu(OtBu)-OH, Fmoc-Ala-OH, Fmoc-Asn(Trt)-OH, Fmoc-Ile-OH, Fmoc-Gly -OH, Fmoc-Ser(tBu)-OH, Fmoc-Leu-OH, Fmoc-Leu-OH, Fmoc-Gly-OH, Palmitoyl chloride, washed with DMF, DCM, methanol in turn after the s...

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Abstract

The invention discloses a polypeptide analogue and a preparation method and application thereof, a core peptide sequence of the polypeptide analogue is OA-GL12, and the core peptide is modified by one or more of the following steps: 1) extending at the N terminal of the core peptide, extending peptide is Cys, and the extending peptide Cys and the core peptide Cys form a disulfide bond; (2) carrying out O-glycosylation modification on the core peptide; 3) carrying out fatty acid modification on the N terminal of the core peptide; and 4) fusing SYN-AKE at the tail end of the core peptide C. The Cyclic-GC12 subjected to cyclization modification is not easy to oxidize and is good in stability; glyco-GC12 subjected to glycosylation modification has better skin absorptivity, so that the Glyco-GC12 can be used for preparing the skin care product; the transdermal effect of the long-chain fatty acid modified Pal-GC12 is enhanced, and the stability is better; the SYN-AKE-GC12 fused by the SYN-AKE-GC12, the SYN-AKE-GC12, the SYN-AKE-GC12 and the

Description

technical field [0001] The invention belongs to the field of biomedicine and medical beauty cosmetics, relates to the field of compounds and products used in the field of human skin repair, and in particular relates to a polypeptide analog and a preparation method and application thereof. Background technique [0002] The skin is the largest organ covering the surface of the human body. It is the physical barrier between the internal environment and the external environment. It plays an important role in protecting the body against external pathogenic microorganisms and maintaining a stable water content. As the organism's first line of defense against external environmental aggression, the skin plays a vital role as a barrier. At the same time, the skin has become the tissue organ most vulnerable to external damage. Skin trauma is a common injury in daily life. form. Skin wounds in some cases (eg diabetes, infection, neuropathy, etc.) delay the wound healing process and mo...

Claims

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Application Information

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IPC IPC(8): C07K7/08C07K19/00C07K1/04C07K1/06A61K38/10A61K8/64A61P17/02A61Q19/00A23L33/18
CPCC07K7/08C07K5/0202A61K8/64A61Q19/00A61P17/02A23L33/18A61K2800/10A61K38/00A23V2002/00A23V2200/318A23V2250/55Y02P20/55
Inventor 王宇恩张凌云周迎春马亚平
Owner 深圳深创生物药业有限公司
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