ENZYMATIC REGIOSELECTIVE AND DIASTEREOSELECTIVE HYDROLYSIS OF PERACETYLATED GLYCEROL-BETA-GLUCOSIDES AND ERYTHRITOL-BETA-GLUCOSIDES

被引:6
作者
SORIENTE, A
DEROSA, M
TRINCONE, A
SODANO, G
机构
[1] UNIV SALERNO, DIPARTIMENTO CHIM, I-84081 BARONISSI, ITALY
[2] CNR, IST CHIM MOLEC INTERESSE BIOL, I-80072 Arco Felice Napoli, ITALY
关键词
D O I
10.1016/0960-894X(95)00402-F
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Diastereomeric O-beta-glucosides at the primary carbons of glycerol and erythritol have been subjected as their peracetates to enzymatic hydrolysis by PFL. Only acetyl groups of the aglycones are hydrolyzed, the diastereoselectivity being very high on the erythritol derivatives and fair on the glycerol derivatives. The chemical synthesis of (2S,3R)-1-(O-beta-D-glucopyranosyl)-butane-2,3,4-triol heptaacetate is also reported.
引用
收藏
页码:2321 / 2324
页数:4
相关论文
共 14 条
  • [1] REGIODIASTEREOSELECTIVE AND DIASTEREOSELECTIVE LIPASE-CATALYZED PREPARATION OF ACETYLATED 2-O-GLUCOSYLGLYCEROLS
    COLOMBO, D
    RONCHETTI, F
    SCALA, A
    TAINO, IM
    ALBINI, FM
    TOMA, L
    [J]. TETRAHEDRON-ASYMMETRY, 1994, 5 (07) : 1377 - 1384
  • [2] CHEMISTRY OF GLYCOSIDIC LINKAGE - EFFICIENT SYNTHESIS OF 1,2-TRANS-DISACCHARIDES
    HANESSIAN, S
    BANOUB, J
    [J]. CARBOHYDRATE RESEARCH, 1977, 53 (01) : C13 - C16
  • [3] HSIAO KF, 1994, BIOORG MED CHEM LETT, V4, P1629
  • [4] GLYCEROL GLUCOSIDES IN THE LILIUM GENUS .3. LILIOSIDES-D AND LILIOSIDES-E 2 GLYCEROL GLUCOSIDES FROM LILIUM-JAPONICUM
    KANEDA, M
    KOBAYASHI, K
    NISHIDA, K
    KATSUTA, S
    [J]. PHYTOCHEMISTRY, 1984, 23 (04) : 795 - 798
  • [5] GLYCEROL GLUCOSIDE IN THE LILLIUM GENUS .2. LILIOSIDE-C, A GLYCEROL GLUCOSIDE FROM LILIUM-LANCIFOLIUM
    KANEDA, M
    MIZUTANI, K
    TANAKA, K
    [J]. PHYTOCHEMISTRY, 1982, 21 (04) : 891 - 893
  • [6] SYNTHESIS OF PROTECTED CARBOHYDRATE-DERIVATIVES THROUGH HOMOLOGATION OF THREOSE AND ERYTHROSE DERIVATIVES WITH CHIRAL GAMMA-ALKOXY ALLYLIC STANNANES
    MARSHALL, JA
    SELETSKY, BM
    LUKE, GP
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) : 3413 - 3420
  • [7] ENZYMATIC PREPARATION OF ENANTIOMERICALLY PURE ALKAN-2-OLS AND ALKAN-3-OLS BY LIPASE-CATALYZED HYDROLYSIS WITH PSEUDOMONAS-CEPACIA IN THE PRESENCE OF ORGANIC MEDIA
    NAOSHIMA, Y
    KAMEZAWA, M
    TACHIBANA, H
    MUNAKATA, Y
    FUJITA, T
    KIHARA, K
    RAKU, T
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (05): : 557 - 561
  • [8] REGALOSIDE-A AND REGALOSIDE-B, ACYLATED GLYCEROL GLUCOSIDES FROM LILIUM-REGALE
    SHIMOMURA, H
    SASHIDA, Y
    MIMAKI, Y
    IIDA, N
    [J]. PHYTOCHEMISTRY, 1988, 27 (02) : 451 - 454
  • [9] ENZYME-CATALYZED SYNTHESIS OF CARBOHYDRATES
    TOONE, EJ
    SIMON, ES
    BEDNARSKI, MD
    WHITESIDES, GM
    [J]. TETRAHEDRON, 1989, 45 (17) : 5365 - 5422
  • [10] CHEMOENZYMATIC SYNTHESIS AND STEREOCHEMISTRY OF ALEPPOTRIOLOSIDE, A NATURALLY-OCCURRING GLUCOSIDE
    TRINCONE, A
    PAGNOTTA, E
    SODANO, G
    [J]. TETRAHEDRON LETTERS, 1994, 35 (09) : 1415 - 1416