Divergent synthesis of all possible optically active regioisomers of Myo-inositol mono- and bisphosphates

被引：3

作者：

Seo, Kyung-Chang ^{[1
]}

Yu, Seok-Ho ^{[1
]}

Chung, Sung-Kee ^{[1
]}

机构：

[1] Pohang Univ Sci & Technol, Dept Chem, Pohang 790784, South Korea

来源：

JOURNAL OF CARBOHYDRATE CHEMISTRY | 2007年 / 26卷 / 5-6期

关键词：

Myo-inositol; inositol phosphates; divergent synthesis; protecting groups; phosphorylation;

D O I：

10.1080/07328300701540225

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：

All possible optically active regioisomers of myo- inositol mono- and bisphosphates were synthesized using inositol derivatives suitably protected with various protecting groups (IR(n)s) as key intermediates. A series of procedures including Novozym 435 catalyzed enzymatic resolution of (3aR, 4S, 7S, 7aR)-rel-3a, 4,7,7a-tetrahydro- 2,2-dimethyl- 1,3- benzodioxole-4,7- diol diacetate, several protection and deprotection reactions, and acyl migration afforded two enantiomeric pairs of IR5 and six enantiomeric pairs of IR4. Phosphorylation of these key intermediates by the phosphitylation and oxidation procedure gave the target products after removal of the protecting groups. [GRAPHICS]

引用

页码：305 / 327

页数：23

共 29 条

[21] Facile syntheses of all possible diastereomers of conduritol and various derivatives of inositol stereoisomers in high enantiopurity from myo-inositol
Kwon, YU
Lee, C
Chung, SK
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (10): : 3327 - 3338
[22] Synthesis of analogs of myo-inositol tetrakisphosphates: Possible stimulus in CF airway epithelial cells.
Freeman, S
Martin, PM
[J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U271 - U271
[23] AN EFFICIENT SYNTHESIS OF OPTICALLY-ACTIVE D-MYO-INOSITOL 1,4,5-TRIPHOSPHATE
LIU, YC
CHEN, CS
[J]. TETRAHEDRON LETTERS, 1989, 30 (13) : 1617 - 1620
[24] Synthesis of 2-deoxy-2-C-alkylglucosides of myo-inositol as possible inhibitors of a N-deacetylase enzyme in the biosynthesis of mycothiol
Gammon, DW
Hunter, R
Steenkamp, DJ
Mudzunga, TT
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (12) : 2045 - 2049
[25] Synthesis of D- and L-myo-inositol 1,2,4,6-tetrakisphosphate, regioisomers of myo-inositol 1,3,4,5 tetrakisphosphate:: activity against Ins(1,4,5)P3 binding proteins
Mills, SJ
Backers, K
Erneux, C
Potter, BVL
[J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (20) : 3546 - 3556
[26] SYNTHESIS OF OPTICALLY-ACTIVE 2,3,6-TRI-O-BENZYL-D-MYO-INOSITOL FROM D-GLUCOSE
SATO, K
SAKUMA, S
MURAMATSU, S
BOKURA, M
[J]. CHEMISTRY LETTERS, 1991, (08) : 1473 - 1474
[27] Efficient routes to optically active azido-, amino-, di-azido- and di-amino-cyclitols with chiro- and allo-configuration from myo-inositol
Sureshan, KM
Ikeda, K
Asano, N
Watanabe, Y
[J]. TETRAHEDRON LETTERS, 2004, 45 (45) : 8367 - 8370
[28] Synthesis of three enantiomeric pairs of scyllo-inositol phosphate and molecular interactions between all possible regioisomers of scyllo-inositol phosphate and inositol 1,4,5-trisphosphate 3-kinase
Kwon, YU
Im, J
Choi, G
Kim, YS
Choi, KY
Chung, SK
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2003, 13 (18) : 2981 - 2984
[29] A SHORT STEP SYNTHESIS OF OPTICALLY-ACTIVE MYOINOSITOL 1,3,4,5-TETRAKIS(PHOSPHATE) AND MYOINOSITOL 1,4,5-TRIS(PHOSPHATE) FROM 1,3,5-TRI-O-BENZOYL-MYO-INOSITOL
WATANABE, Y
FUJIMOTO, T
SHINOHARA, T
OZAKI, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (06) : 428 - 429

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