Chitin ester derivatives

Ester derivatives of cellulose, chitin, dextran, amylose, and amylopectin were prepared utilizing the acid chloride derivatives described in Part B of the Experimental Section. 

Table I lists physical data for a number of the carbamate and ester derivatives of cellulose, chitin, amylose, amylopectin, and dextran synthesized as described in the Experimental Section. The solubility of the polysaccharide starting materials as well as that of the produced derivatives allows for macromolecular characterization through techniques including UV, NMR, IR, high pressure liquid chromatography, etc.

Derivatives (Table I) formed by the reaction of the chosen polysaccharide with an isocyanate or acid chloride are carbamates and esters respectively. However, chitin or poly[(1+4)(N-acetyl-2-amino-2-deoxy-f3-glucopyranose)] actually used in this experiment contains approximately 16% free amine groups which can form urea and amide derivatives with the above reagents. 

Derivatives of chitin, ethers, esters, and a sodio derivative, have been discussed, and the carboxymethyl ether of chitin has been prepared by the standard method of carboxymethylation. ... 

A number of nikkomycin analogues of type 171 have been prepared by acylation of uracil polyoxin C with aminoacid units, using iV-hydroxysuc-cinimidyl esters as intermediates. The best inhibitory activity against fungal chitin synthase was found for cases in which the aminoacid was an 5-arylmethyl derivative of L-cysteine or penicillamine. ... 

Analogues 249 (X = H, OH) of UDP-GlcNAc have been prepared as potential inhibitors of chitin synthetases. The synthetic route involved a C-allyl derivative of GlcNAc, which was elaborated by ozonolysis, Wittig reaction and coupling with the nucleoside, followed by hydrogenation or hydroxylation as appropriate. The corresponding amides were also prepared from 5 -amino-5 -deoxyuridine. Lipophilic amino acid methyl esters and methylamides have been coupled to 0-5 of AZT by carbamate links. The products showed anti-HIV activity, but this was not due to carbamate hydrolysis or to direct inhibition of reverse transcriptase, and the mechanism of action may be one not previously observed with nucleoside antivirals. ... 

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