Cluster peptide provided with UCST behavior and methyloic side chain and preparation method thereof
A technology of clustering peptides and carboxyl groups, which is applied in the field of preparation of ionic clustering peptide homopolymers, and achieves the effects of simple equipment, readily available raw materials, and easy operation
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Embodiment 1
[0049] Preparation of clustering peptides shown in embodiment 1, formula (III)
[0050]
[0051] (1) Add 180g (1.2mol, 50% glyoxylic acid aqueous solution) of glyoxylic acid into a 1000mL round bottom flask, then add 600mL of dichloromethane, slowly add 45mL (0.6mol) dropwise while stirring with a syringe Allylamine, reacted at room temperature for 4 hours. After the reaction was completed, dichloromethane was removed by rotary evaporation, and 600 mL of hydrochloric acid (2 mol / L) was added to reflux at 110° C. for 18 hours. After the solvent was removed by rotary evaporation, 90mL of methanol was added to fully dissolve, and then 700mL of tetrahydrofuran was added and placed in a refrigerator at minus 20°C for recrystallization overnight. The crystals were filtered and dried to obtain (64.3 g, yield 70.6%) N-allyl substituted glycine hydrochloride. H NMR 1 H NMR (500MHz,D 2 O)δ: 5.81 (m, 1H), 5.43 (t, 2H), 3.79 (s, 2H), 3.64 (d, 2H). H NMR spectrum see figure 1 .
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Embodiment 2
[0057] Preparation of clustering peptides shown in embodiment 2, formula (IV)
[0058]
[0059] (1) Add 180g (1.2mol, 50% glyoxylic acid aqueous solution) of glyoxylic acid into a 1000mL round bottom flask, then add 600mL of dichloromethane, slowly add 40mL (0.6mol) dropwise while stirring with a syringe Propargylamine, reacted at room temperature for 6 hours. After the reaction was completed, dichloromethane was removed by rotary evaporation, and 300 mL of hydrochloric acid (4 mol / L) was added to reflux at 110° C. for 24 hours. After the solvent was removed by rotary evaporation, 90mL of methanol was added to fully dissolve, and then 700mL of tetrahydrofuran was added and placed in a refrigerator at minus 20°C for recrystallization overnight. The crystals were filtered and dried to obtain (55.9 g, yield 62.9%) N-propargyl substituted glycine hydrochloride. 1H NMR (500MHz, D2O): δ3.72(d, 2H), 3.71(t, 2H), 2.71(t, 1H). H NMR spectrum see attached image 3
[0060](2) 30...
Embodiment 3
[0065] Example 3, preparing other clustering peptides with different degrees of polymerization, the synthesis method is the same as above, but the amount of initiator is different
[0066] Polypeptide (III)-2, the experimental procedure is the same as in Example 1, except that the amount of initiator is changed to 26 microliters (in this system, the molar ratio of benzylamine and the white crystal obtained in step (3) is 1 :40)
[0067] Polypeptide (III)-3, the experimental procedure is the same as in Example 1, except that the amount of initiator is changed to 52 microliters (in this system, the molar fraction ratio of benzylamine and the white crystal obtained in step (3) is 1 :20)
[0068] Polypeptide (IV)-2, the experimental procedure is the same as in Example 2, except that the amount of initiator is changed to 13 microliters (in this system, the molar fraction ratio of benzylamine and the white crystal obtained in step (3) is 1 :80)
[0069] Polypeptide (IV)-3, the ex...
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