Synthesis of a chitosan tetramer derivative, beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-D-Glc N through a partial N-acetylation reaction by chitin deacetylase.
We have synthesized beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-beta-D-GlcNAc-(1-->4)-D-GlcN (2) through a partial N-acetylation reaction of chitosan tetramer 1 by a chitin deacetylase from Colletotrichum lindemuthianum ATCC 56676. The compound was purified from the mixture of acetylation products of 1 using cation-exchange column chromatography and amine-adsorption column chromatography, and its structure was estimated by 1H NMR and FABMS analyses. The enzymatic reaction allows a regioselectivity that is hard to achieve by chemical N-acetylation.
Tokuyasu
K
K
National Food Research Institute, Tsukuba, Ibaraki, Japan. tokuyasu@nfri.affrc.go.jp
Ono
H
H
Mitsutomi
M
M
Hayashi
K
K
Mori
Y
Y
D000107:Acetylation; D000581:Amidohydrolases / Q000737:chemistry*; D002240:Carbohydrate Sequence; D002686:Chitin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D048271:Chitosan; D020231:Colletotrichum / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008969:Molecular Sequence Data; D013997:Time Factors
C410296:GlcNAc-(1-4)-GlcNAc-(1-4)-GlcNAc-(1-4)-GlcN; D002686:Chitin; D048271:Chitosan; D000581:Amidohydrolases; C019866:chitin deacetylase