A long-acting hypoglycemic and weight-reducing peptide, its preparation method and application
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A technology of compound and peptide resin, applied in the field of long-acting oxyntomodulin hybrid peptide, which can solve the problems of short half-life and weak hypoglycemic activity
Active Publication Date: 2021-08-06
CHINA PHARM UNIV
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Compared with pure GLP-1R agonists, OXM has a better effect in intervening body weight, regulating lipid metabolism, and improving glucose tolerance, but its hypoglycemic activity is relatively weak and its half-life is short
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Embodiment 1
[0080]
[0081] solid phase synthesis
[0082] 1. Synthesis of polypeptide backbone
[0083] 1.1 Resin swelling
[0084] Weigh 50mg of Fmoc-Rink amide-MBHA Resin (degree of substitution: 0.4mmol / g), swell with 7mL of DCM for 30min, filter to remove DCM, then swell with 10mL of NMP for 30min, rinse with NMP and 7mL of DCM respectively.
[0085] 1.2 Removal of Fmoc protecting group
[0086] Put the swollen resin into the reactor, add 25% piperidine / NMP (V / V) solution containing 0.1M HOBt to the resin to remove Fmoc, and wash it with NMP after the reaction. A resin free of the initially attached Fmoc protecting group is obtained.
[0087] 1.3 Synthesis of Fmoc-Ser(tBu)-Rink amide-MBHA Resin
[0088] Fmoc-Ser(tBu)-OH (15.4 mg, 0.04 mmol), HBTU (15.1 mg, 0.04 mmol), HOBt (5.4 mg, 0.04 mmol) and DIPEA (13.9 μL, 0.08 mmol) were dissolved in NMP 10 mL, and then This solution was added to the resin obtained in the previous step to react for 2 hours, after which the reaction solut...
Embodiment 2
[0096]
[0097] The synthesis method was the same as in Example 1, and the collected solution was lyophilized to obtain 29.9 mg of pure product. The theoretical relative molecular mass is 4662.3. ESI-MS m / z: Calcd.[M+3H] 3+ 1555.1, [M+4H] 4+ 1166.6; Found[M+3H] 3+ 1555.7, [M+4H] 4+ 1166.1.
Embodiment 3
[0099]
[0100] The synthesis method was the same as in Example 1, and the collected solution was lyophilized to obtain 30.4 mg of the pure product. The theoretical relative molecular mass is 4621.2. ESI-MS m / z: Calcd.[M+3H] 3+ 1541.4, [M+4H] 4+ 1156.3; Found[M+3H] 3+ 1541.9, [M+4H] 4+ 1156.7.
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Abstract
The invention relates to a long-acting hypoglycemic and weight-reducing gastric oxyntomodulin (OXM) hybrid peptide and its application and synthesis method. By modifying OXM, hybridizing with the peptide sequence of Exenatide, and conjugating small molecular fatty chains, the OXM hybrid peptide with longer pharmacological action time and better weight loss effect is obtained. The synthesis of the target polypeptide is quickly achieved by solid-phase synthesis, and the crude product is purified and freeze-dried to obtain the target compound.
Description
technical field [0001] The invention relates to the field of medicinal chemistry, in particular to long-acting oxyntomodulin (OXM) hybrid peptide and application thereof. Background technique [0002] The cause of metabolic syndrome is abnormal metabolism of various substances such as protein, fat and carbohydrates. Overnutrition and reduced physical activity can lead to obesity and obesity-related diseases such as diabetes. In recent years, the incidence of type 2 diabetes and dyslipidemia has been increasing day by day. [0003] Oxyntomodulin (OXM) is a polypeptide composed of 37 amino acids secreted by small intestinal L cells, including the entire 29 amino acid sequence of glucagon and the 8 amino acid part of the C-terminal extension, which is similar to glucagon Peptide-1 (GLP-1) has 50% homology, and the peptide sequence is: HSQGTFTSDYSKYLDSRRAQDFVQWLMNTKRNRNNIA. OXM can simultaneously activate glucagon-like peptide-1 receptor (GLP-1R) and glucagon receptor (GCGR),...
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