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

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1995年 / 5卷 / 20期

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.

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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 [J].

COLOMBO, D ;

RONCHETTI, F ;

SCALA, A ;

TAINO, IM ;

ALBINI, FM ;

TOMA, L .

TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1377-1384

[2] CHEMISTRY OF GLYCOSIDIC LINKAGE - EFFICIENT SYNTHESIS OF 1,2-TRANS-DISACCHARIDES [J].

HANESSIAN, S ;

BANOUB, 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 [J].

KANEDA, M ;

KOBAYASHI, K ;

NISHIDA, K ;

KATSUTA, S .

PHYTOCHEMISTRY, 1984, 23 (04) :795-798

[5] GLYCEROL GLUCOSIDE IN THE LILLIUM GENUS .2. LILIOSIDE-C, A GLYCEROL GLUCOSIDE FROM LILIUM-LANCIFOLIUM [J].

KANEDA, M ;

MIZUTANI, K ;

TANAKA, K .

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 [J].

MARSHALL, JA ;

SELETSKY, BM ;

LUKE, GP .

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 [J].

NAOSHIMA, Y ;

KAMEZAWA, M ;

TACHIBANA, H ;

MUNAKATA, Y ;

FUJITA, T ;

KIHARA, K ;

RAKU, T .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (05) :557-561

[8] REGALOSIDE-A AND REGALOSIDE-B, ACYLATED GLYCEROL GLUCOSIDES FROM LILIUM-REGALE [J].

SHIMOMURA, H ;

SASHIDA, Y ;

MIMAKI, Y ;

IIDA, N .

PHYTOCHEMISTRY, 1988, 27 (02) :451-454

[9] ENZYME-CATALYZED SYNTHESIS OF CARBOHYDRATES [J].

TOONE, EJ ;

SIMON, ES ;

BEDNARSKI, MD ;

WHITESIDES, GM .

TETRAHEDRON, 1989, 45 (17) :5365-5422

[10] CHEMOENZYMATIC SYNTHESIS AND STEREOCHEMISTRY OF ALEPPOTRIOLOSIDE, A NATURALLY-OCCURRING GLUCOSIDE [J].

TRINCONE, A ;

PAGNOTTA, E ;

SODANO, G .

TETRAHEDRON LETTERS, 1994, 35 (09) :1415-1416