SYNTHESIS OF (2S,2'R,3R,4E,8E)-N-2'-HYDROXYOCTADECANOYL-1-O-(BETA-D-GLUCOPYRANOSYL)-9-METHYL-4,8-SPHINGADIENINE (PEN-III), A CEREBROSIDE ISOLATED FROM PENICILLIUM-FUNICULOSUM AS THE FRUITING INDUCER AGAINST SCHIZOPHYLLUM-COMMUNE

被引：9

作者：

ABE, T ^{[1
]}

MORI, K ^{[1
]}

机构：

[1] UNIV TOKYO, DEPT AGR CHEM, BUNKYO KU, TOKYO 113, JAPAN

来源：

BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY | 1994年 / 58卷 / 09期

关键词：

D O I：

10.1271/bbb.58.1671

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

(2S,2'R,3R,4E,8E)-N-2'-Hydroxyoctadecanoyl-1-O-(beta-D-glucopyranosyl)-9-methyl-4,8-sphingadienine (Pen III), a cerebroside isolated from Penicillium funiculosum A-1 as the fruiting inducer against Basidiomycete Schizophyllum commune, was synthesized by starting from D-glucose, L-serine, homoprenyl acetate and stearic acid.

引用

页码：1671 / 1674

页数：4

共 9 条

[1] Synthesis of sphingosine relatives .17. Synthesis of (2S,2'R,3R,3'E,4E,8E)-1-O-(beta-D-glucopyranosyl)-N-(2'-hydroxy-3'-octadecenoyl)-9-methyl-4,8-sphingadienine (Pen II), the major cerebroside isolated from Penicillium funiculosum as the fruiting-inducer against Schizophyllum commune
Mori, K
Uenishi, K
LIEBIGS ANNALEN, 1996, (01): : 1 - 6
[2] SYNTHESIS OF SPHINGOSINE RELATIVES .3. SYNTHESIS OF (4E,8E,2S,3R,2'R)-N-2'-HYDROXYHEXADECANOYL-1-O-BETA-D-GLUCOPYRANOSYL-9-METHYL-4,8-SPHINGADIENINE, THE FRUITING-INDUCING CEREBROSIDE IN A BASIDIOMYCETE SCHIZOPHYLLUM-COMMUNE
MORI, K
FUNAKI, Y
TETRAHEDRON, 1985, 41 (12) : 2379 - 2386
[3] SYNTHESIS OF (2S,3R,4E,8E)-N-(2'R)-2'-HYDROXYHEXADECANOYL-9-METHYL-4,8-SPHINGADIENINE, THE CERAMIDE PORTION OF THE FRUITING-INDUCING CEREBROSIDE IN A BASIDIOMYCETE SCHIZOPHYLLUM-COMMUNE
MORI, K
FUNAKI, Y
TETRAHEDRON LETTERS, 1984, 25 (46) : 5291 - 5294
[4] SYNTHESIS OF SPINGOSINE RELATIVES .4. SYNTHESIS AND BIOLOGICAL-ACTIVITY OF THE ISOMERS AND ANALOGS OF (4E,8E,2S,3R,2'R)-N-2'-HYDROXYHEXADECANOYL-9-METHYL-4,8-SPHINGADIENINE, THE CERAMIDE PORTION OF THE FRUITING-INDUCING CEREBROSIDE IN A BASIDIOMYCETE SCHIZOPHYLLUM-COMMUNE
FUNAKI, Y
KAWAI, G
MORI, K
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1986, 50 (03): : 615 - 623
[5] SYNTHESIS OF SPHINGOSINE RELATIVES .2. SYNTHESIS OF (4E,8E,2S,3R,2'R)-N-2'-HYDROXYHEXADECANOYL-9-METHYL-4,8-SPHINGADIENINE, THE CERAMIDE PORTION OF THE FRUITING-INDUCING CEREBROSIDE IN A BASIDIOMYCETE SCHIZOPHYLLUM-COMMUNE, AND ITS (2R,3S)-ISOMER
MORI, K
FUNAKI, Y
TETRAHEDRON, 1985, 41 (12) : 2369 - 2377
[6] Synthesis of (2S,3R,4E,8E)-9-methyl-4,8-sphingadienine via a novel SN2′ type reaction mediated by a thioether carbanion
Wang, XZ
Wu, YL
Jiang, SD
Singh, G
TETRAHEDRON LETTERS, 1999, 40 (50) : 8911 - 8914
[7] SYNTHESIS OF SPHINGOSINE RELATIVES .10. SYNTHESIS OF (2S,3R,4E)-1-O-(BETA-D-GLUCOPYRANOSYL)-N-[30'-(LINOLEOYLOXY)TRIACONTANOYL]-4-ICOSASPHINGENINE, A NEW ESTERIFIED CEREBROSIDE ISOLATED FROM HUMAN AND PIG EPIDERMIS
MORI, K
MATSUDA, H
LIEBIGS ANNALEN DER CHEMIE, 1991, (06): : 529 - 535
[8] SYNTHESIS OF SPHINGOSINE RELATIVES .9. SYNTHESIS OF (2S,3R,4E)-1-O(BETA-D-GLUCOPYRANOSYL)-N-[24-(LINOLEOYLOXY)TETRACOSANOYL]-4-SPHINGENINE - THE STRUCTURE PROPOSED FOR THE ESTERIFIED CEREBROSIDE IN THE EPIDERMIS OF GUINEA-PIGS
MORI, K
NISHIO, H
LIEBIGS ANNALEN DER CHEMIE, 1991, (03): : 253 - 257
[9] SYNTHETIC STUDIES ON CELL-SURFACE GLYCANS .42. TOTAL SYNTHESIS OF CEREBROSIDES - (2S, 3R, 4E)-1-O-BETA-D-GALACTOPYRANOSYL-N-(2'R AND 2'S)-2'-HYDROXYTETRACOSANOYLSPHINGENINE
KOIKE, K
SUGIMOTO, M
NAKAHARA, Y
OGAWA, T
CARBOHYDRATE RESEARCH, 1987, 162 (02) : 237 - 246

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