We prepared the penta-N-acetyl-chitopentaose 2 by using recombinant Escherichia coli (E. coli) strains harboring the nodC gene (encoding chitooligosaccharide synthase) from Azorhizobium caulinodans. The deacetylase NodB removed the N-acetyl moiety from the nonreducing terminus of 2 to give tetra-N-acetyl-chitopentaose 3. N-Acylation of 3 with stearyl chloride was performed in DMF containing water and provided the corresponding lipo-chitopentaose nodulation factor 4.
Keywords: Lipo-chitopentaose nodulation factor, chemo-enzymatic synthesis, degradation velocity, chitinase
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