Isomerization of all-(E)-Retinoic Acid Mediated by Carbodiimide Activation - Synthesis of ATRA Ether Lipid Conjugates

被引：14

作者：

Christensen, Mikkel S. ^{[1
]}

Pedersen, Palle J. ^{[1
]}

Andresen, Thomas L. ^{[2
]}

Madsen, Robert ^{[1
]}

Clausen, Mads H. ^{[1
]}

机构：

[1] Tech Univ Denmark, Dept Chem, DK-2800 Lyngby, Denmark

[2] Tech Univ Denmark, Dept Micro & Nanotechnol, DK-4000 Roskilde, Denmark

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 2010卷 / 04期

关键词：

Phospholipids; Retinoic acid; Acylation; Mitsunobu reaction; Isomerization; RETINOIC ACID; PHOSPHOLIPASE-A2; RELEASE;

D O I：

10.1002/ejoc.200901128

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学];

摘要：

Treatment of the lysolipid 1-O-hexadecyl-sn-phosphatidylcholine with all-(E)-retinoic acid, DCC and DMAP resulted in poor acylation and caused (Z)/(E) isomerization of the alpha-beta double bond. In the presence of a proton source, the carbodiimide-activated all-(E)-retinoic acid undergoes fast isomerization to give a final mixture of (13E)/(13Z) isomers in a 3:1 ratio. Similar treatment of (13Z)-retinoic acid leads to the same isomer ratio. The isomerization was circumvented successfully by using a Mitsunobu reaction, which provided an efficient synthesis of all-(E)-retinoic acid sn-2-conjugated to phosphatidylcholine and phosphatidylglycerol etherlipids.

引用

页码：719 / 724

页数：6

共 21 条

[1]

Synthesis of anti-tumour phosphatidylinositol analogues from glucose by the use of ring-closing olefin metathesis [J].

Andresen, TL ;

Skytte, DM ;

Madsen, R .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (20) :2951-2957

[2]

Enzymatic release of antitumor ether lipids by specific phospholipase A2 activation of liposome-forming prodrugs [J].

Andresen, TL ;

Davidsen, J ;

Begtrup, M ;

Mouritsen, OG ;

Jorgensen, K .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (07) :1694-1703

[3]

13-cis retinoic acid and isomerisation in paediatric oncology -: is changing shape the key to success? [J].

Armstrong, JL ;

Redfern, CPF ;

Veal, GJ .

BIOCHEMICAL PHARMACOLOGY, 2005, 69 (09) :1299-1306

[4]

PROTON-TRANSFER STEPS IN STEGLICH ESTERIFICATION - A VERY PRACTICAL NEW METHOD FOR MACROLACTONIZATION [J].

BODEN, EP ;

KECK, GE .

JOURNAL OF ORGANIC CHEMISTRY, 1985, 50 (13) :2394-2395

[5]

Glutathione S-transferases act as isomerases in isomerization of 13-cis-retinoic acid to all-trans-retinoic acid in vitro [J].

Chen, H ;

Juchau, MR .

BIOCHEMICAL JOURNAL, 1997, 327 :721-726

[6]

Self-organizing properties of natural and related synthetic glycolipids [J].

Dumoulin, F ;

Lafont, D ;

Boullanger, P ;

Mackenzie, G ;

Mehl, GH ;

Goodby, JW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (46) :13737-13748

[7]

INHIBITION OF HUMAN NON-PANCREATIC PHOSPHOLIPASES-A2 BY RETINOIDS AND FLAVONOIDS - MECHANISM OF ACTION [J].

FAWZY, AA ;

VISHWANATH, BS ;

FRANSON, RC .

AGENTS AND ACTIONS, 1988, 25 (3-4) :394-400

[8]

Retinoids in cancer therapy and chemoprevention: promise meets resistance [J].

Freemantle, SJ ;

Spinella, MJ ;

Dmitrovsky, E .

ONCOGENE, 2003, 22 (47) :7305-7315

[9]

Synthesis of naturally occurring phosphatidylinositol 3,4,5-trisphosphate [PtdIns(3,4,5)P3] and its diastereoisomers [J].

Gaffney, PRJ ;

Reese, CB .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (02) :192-205

[10]

A macrolactonization-based strategy to obtain microtuble-stabilizing agent (-)-laulimalide [J].

Ghosh, AK ;

Wang, Y .

TETRAHEDRON LETTERS, 2001, 42 (20) :3399-3401

← 1 2 3 →