FORMATION OF 11-TRANS SLOW REACTING SUBSTANCES

被引：10

作者：

ATRACHE, V ^{[1
]}

SOK, DE ^{[1
]}

PAI, JK ^{[1
]}

SIH, CJ ^{[1
]}

机构：

[1] UNIV WISCONSIN, SCH PHARM, MADISON, WI 53706 USA

来源：

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES | 1981年 / 78卷 / 03期

关键词：

D O I：

10.1073/pnas.78.3.1523

中图分类号：

Q [生物科学];

学科分类号：

07 ; 0710 ; 09 ;

摘要：

Under strongly basic conditions [excess LiOH, dimethoxyethane/water (4:1, vol/vol)], purified slow reacting substances (SRS) SRS-GSH and SRS-Cys were not isomerized to their corresponding 11-trans isomers. Addition of thiols such as glutathione (GSH) or L-cysteine to this basic medium produced various amounts of 11-trans-SRS, depending on the thiol concentration. This chemical isomerization was inhibited by the radical scavenger 4-hydroxy-2,2,6,6-tetramethylpiperidinooxy free radical (HTMP); the inhibition suggests that the thiyl radical is added reversibly to the triene system at C-12, resulting in the overall cis .fwdarw. trans isomerization of the 11,12 double bond. Because the amount of 11-trans-SRS-Cys produced by intact RBL-1 cells apparently contain enzymes systems that form peroxides, which enhance the formation of thiyl radicals, required for cis .fwdarw. trans isomerization. HTMP inhibited the formation of 11-trans-SRS-Cys in this cell system.

引用

页码：1523 / 1526

页数：4

共 16 条

[1] 11-TRANS LEUKOTRIENE-C - A NATURALLY-OCCURRING SLOW REACTING SUBSTANCE
CLARK, DA
GOTO, G
MARFAT, A
COREY, EJ
HAMMARSTROM, S
SAMUELSSON, B
[J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1980, 94 (04) : 1133 - 1139
[2] TOTAL SYNTHESIS OF SLOW REACTING SUBSTANCES (SRS) - LEUKOTRIENE C-2 (11-TRANS-LEUKOTRIENE-C)-(3) AND LEUKOTRIENE-D-(4)
COREY, EJ
CLARK, DA
MARFAT, A
GOTO, G
[J]. TETRAHEDRON LETTERS, 1980, 21 (33) : 3143 - 3146
[3] STEREOSPECIFIC TOTAL SYNTHESIS OF A SLOW REACTING SUBSTANCE OF ANAPHYLAXIS, LEUKOTRIENE C-1
COREY, EJ
CLARK, DA
GOTO, G
MARFAT, A
MIOSKOWSKI, C
SAMUELSSON, B
HAMMARSTROM, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (04) : 1436 - 1439
[4] TRANSLOCATION OF INTRACELLULAR GLUTATHIONE TO MEMBRANE-BOUND GAMMA-GLUTAMYL TRANSPEPTIDASE AS A DISCRETE STEP IN THE GAMMA-GLUTAMYL CYCLE - GLUTATHIONURIA AFTER INHIBITION OF TRANSPEPTIDASE
GRIFFITH, OW
MEISTER, A
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1979, 76 (01) : 268 - 272
[5] HAMBERG M, 1967, J BIOL CHEM, V242, P5329
[6] STRUCTURE OF LEUKOTRIENE-C IDENTIFICATION OF THE AMINO-ACID PART
HAMMARSTROM, S
MURPHY, RC
SAMUELSSON, B
CLARK, DA
MIOSKOWSKI, C
COREY, EJ
[J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1979, 91 (04) : 1266 - 1272
[7] IDENTIFICATION OF THE SLOW REACTING SUBSTANCES FROM CAT PAWS
HOUGLUM, J
PAI, JK
ATRACHE, V
SOK, DE
SIH, CJ
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1980, 77 (10): : 5688 - 5692
[8] Kharasch M.S., 1938, Chem. Ind, V57, P752
[9] SLOW REACTING SUBSTANCES OF ANAPHYLAXIS - IDENTIFICATION OF LEUKOTRIENES-C-1 AND LEUKOTRIENES-D FROM HUMAN AND RAT SOURCES
LEWIS, RA
AUSTEN, KF
DRAZEN, JM
CLARK, DA
MARFAT, A
COREY, EJ
[J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA-BIOLOGICAL SCIENCES, 1980, 77 (06): : 3710 - 3714
[10] The peroxide effect in the addition of reagents to unsaturated compounds and in rearrangement reactions
Mayo, FR
Walling, C
[J]. CHEMICAL REVIEWS, 1940, 27 (02) : 351 - 412

← 1 2 →