Cationic copolymerized amino acid and preparation method thereof
A cationic, amino acid technology, applied in the production of bulk chemicals, etc., can solve the problems of complex preparation, lack of enzymatic degradation rate, strong cytotoxicity, etc.
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[0032] Further, there is also provided a preparation method of a cationic copolymerized amino acid, comprising the steps:
[0033] (1) Amino acid-NCA and N-substituted glycine-NCA were prepared by reported methods (a.J Polym SciAPolym Chem, 2012, 50, 3743-3749b. Biomacromolecules 2018, 19, 2109-2116);
[0034] (2) Ring-opening polymerization of amino acid-NCA and N-substituted glycine-NCA is initiated by a nucleophile to prepare a cationic copolymerized amino acid.
[0035] In the present invention, firstly, through the method for preparing amino acid N-carboxy intracyclic acid anhydride (namely amino acid-NCA) in the prior art, the corresponding amino acid-NCA and N-substituted glycine-NCA are prepared, and the L-amino acid- The structural formula of NCA is The structural formula of the N-substituted glycine-NCA is Wherein, n is 5-500, m is 5-500, R is one of hydrogen atom, alkyl, substituted alkyl or alkylamino, R' is one of alkyl or substituted alkyl, R and R ' is a di...
Embodiment 1
[0045] Example 1 Synthesis of poly(trifluoroacetyl-L-lysine-co-sarcosine)
[0046] 1.0 g (3.7 mmol) of trifluoroacetyl-L-lysine-NCA, 425 mg (3.7 mmol) of sarcosine-NCA, 16.7 mg (0.1 mmol) of LiHMDS and 20 mL of N'N-dimethylform were added to the reactor After the reaction, the mixture was poured into 100 mL of anhydrous ether for precipitation, filtered, and then vacuum-dried to obtain poly(trifluoroacetyl-L-lysine) acid-co-sarcosine) in 80% yield. The number-average molecular weight of the prepared poly(trifluoroacetyl-L-lysine-co-sarcosine) measured by GPC was 10,000, and the molecular weight distribution was 1.2. figure 2 The hydrogen NMR spectrum (CDCl) of the prepared poly(trifluoroacetyl-L-lysine-co-sarcosine) shown 3 ), it can be proved that poly(trifluoroacetyl-L-lysine-co-sarcosine) is successfully prepared, wherein, after calculation, the unit ratio of trifluoroacetyl-L-lysine is 50%, which is higher than the feeding ratio match.
Embodiment 2
[0047] Example 2 Synthesis of poly(L-lysine-co-sarcosine)
[0048] 0.5 g of poly(trifluoroacetyl-L-lysine-co-sarcosine) (containing 1.6 mmol of amine groups) prepared in Example 1 above, 0.3 g of sodium hydroxide and 20 mL of tetrahydrofuran were added to the reactor. , sealed and placed in an oil bath at 60°C for 12 hours. After the reaction, the mixture was poured into 100 mL of anhydrous ether for precipitation, filtered, and then vacuum-dried to obtain poly(L-lysine-co-sarcosine) ), the yield was 85%. The number average molecular weight of the prepared poly(L-lysine-co-sarcosine) measured by GPC was 8000, and the molecular weight distribution was 1.2.
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