672309-02-3Relevant academic research and scientific papers
Deoxy and deoxyfluoro analogues of acetylated methyl β-D- xylopyranoside - Substrates for acetylxylan esterases
Mastihubova, Maria,Biely, Peter
, p. 2101 - 2110 (2007/10/03)
Four modified substrates for acetylxylan esterases, 2-deoxy, 3-deoxy, 2-deoxy-2-fluoro, and 3-deoxy-3-fluoro derivatives of di-O-acetylated methyl β-D-xylopyranoside were synthesized via 2,3-anhydropentopyranoside precursors. Methyl 2,3-anhydro-4-O-benzyl-β-D-ribopyranoside was transformed into methyl 2,3-anhydro-4-O-benzyl-β-D-lyxopyranoside in three steps. The epoxide ring opening of 2,3-anhydropentopyranosides was accomplished either by hydride reduction or hydrofluorination. Methyl β-D-xylopyranoside 2,3,4-tri-O-, 2,4-di-O-, and 3,4-di-O-acetates, and the prepared diacetate analogues were tested as substrates of acetylxylan esterases from Schizophyllum commune and Trichoderma reesei. Measurement of their rate of deacetylation pointed to unique structural requirements of the enzymes for the substrates. The enzymes differed particularly in the requirement for the trans vicinal hydroxy group in the deacetylation at C-2 and C-3 and in the tolerance to the presence of trans vicinal acetyl groups esterifying the OH group at C-2 and C-3.
An efficient chemoenzymatic route to methyl 4-O-benzyl-2,3-anhydro-β- D-lyxopyranoside from methyl β-D-xylopyranoside
Mastihubova, Maria,Mastihuba, Vladimir,Biely, Peter
, p. 425 - 428 (2007/10/03)
Methyl 4-O-benzyl-2,3-anhydro-β-D-lyxopyranoside, an intermediate for the preparation of methyl β-D-xylopyranoside derivatives modified at C-2, was obtained in five steps in 58% yield. The synthetic sequence starts from methyl β-D-xylopyranoside through two main steps involving regioselective enzymatic acetylation and deacetylation catalyzed by lipase PS.
