26528-22-3Relevant 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.
Synthesis of 6-Deoxy and 3,6-Dideoxy Derivatives from Unprotected Glycosides Employing the Mitsunobu Reaction
Dancy, Isabelle,Laupichler, Lothar,Rollin, Patrick,Thiem, Joachim
, p. 343 - 350 (2007/10/02)
Starting with unprotected hexopyranoside derivatives, an efficient synthesis of 6-deoxy- and 3,6-dideoxyhexopyranosides was achieved in two consecutive steps involving a highly regioselective Mitsunobu reaction and subsequent desulfurization. Key Words: Mitsunobu reaction / 6-Thio glycosides / 3,6-Dithio glycosides / 6-Deoxy glycosides / 3,6-Dideoxy glycosides
