The total synthesis of 5-oxo-12(S)-hydroxy-6(E),8(Z),10(E),14(Z)-eicosatetraenoic acid and its 8,9-trans-isomer and their identification in human platelets

被引：14

作者：

Khanapure, SP

Powell, WS

Rokach, J

机构：

[1] Florida Inst Technol, Claude Pepper Inst, Melbourne, FL 32901 USA

[2] Florida Inst Technol, Dept Chem, Melbourne, FL 32901 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1998年 / 63卷 / 24期

关键词：

D O I：

10.1021/jo9813282

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of 5-oxo-12(S)-hydroxy-6(E),8(Z),10(E), 14(Z)-eicosatetraenoic acid (5-oxo-12-HETE) 6 and its 8-trans-isomer 7 is reported. The synthetic 5-oxo-12-HETE 6 and its 8,9-trans-isomer 7 were used to identify their formation in mixtures of platelets and neutrophils by transcellular metabolism.

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页码：8976 / 8982

页数：7

相关论文

共 18 条

[1] STEREOSPECIFIC SYNTHESIS OF LEUKOTRIENE B4 (LTB4) [J].

GUINDON, Y ;

ZAMBONI, R ;

LAU, CK ;

ROKACH, J .

TETRAHEDRON LETTERS, 1982, 23 (07) :739-742

[2] Synthesis of 10,11-dihydro-12-oxo-LTB(4), a key biochemical intermediate [J].

Khanapure, SP ;

Wang, SS ;

Powell, WS ;

Rokach, J .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (02) :325-330

[3] 12-OXO-LTB(4), A KEY PIVOTAL INTERMEDIATE IN LTB(4) METABOLISM [J].

KHANAPURE, SP ;

MANNA, S ;

ROKACH, J ;

MURPHY, RC ;

WHEELAN, P ;

POWELL, WS .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (06) :1806-1813

[4] Total synthesis of a potent proinflammatory 5-oxo-ETE and its 6,7-dihydro biotransformation product [J].

Khanapure, SP ;

Shi, XX ;

Powell, WS ;

Rokach, J .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (02) :337-342

[5]

POWELL WM, UNPUB

[6]

POWELL WS, 1993, J BIOL CHEM, V268, P9280

[7]

Powell WS, 1996, J IMMUNOL, V156, P336

[8]

POWELL WS, 1998, UNPUB BLOOD

[9] THE STEREOSPECIFIC SYNTHESIS OF LEUKOTRIENE-A4 (LTA4), 5-EPI-LTA4, 6-EPI-LTA4 AND 5-EPI,6-EPI-LTA4 [J].

ROKACH, J ;

ZAMBONI, R ;

LAU, CK ;

GUINDON, Y .

TETRAHEDRON LETTERS, 1981, 22 (29) :2759-2762

[10] SYNTHESIS OF LEUKOTRIENES - A NEW SYNTHESIS OF NATURAL LEUKOTRIENE A4 [J].

ROKACH, J ;

YOUNG, RN ;

KAKUSHIMA, M ;

LAU, CK ;

SEGUIN, R ;

FRENETTE, R ;

GUINDON, Y .

TETRAHEDRON LETTERS, 1981, 22 (11) :979-982