CLOSURE OF THE OXIDE BRIDGE IN MORPHINE BIOSYNTHESIS

被引：21

作者：

LENZ, R ^{[1
]}

ZENK, MH ^{[1
]}

机构：

[1] UNIV MUNICH,LEHRSTUHL PHARMAZEUT BIOL,D-80333 MUNICH,GERMANY

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 23期

关键词：

D O I：

10.1016/S0040-4039(00)76696-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly substrate specific enzyme has been discovered and purified to homogeneity, which transfers the acetyl-moiety from acetyl-coenzyme A to the 7-OH group of salutaridinol. The formed 7-O-acetyl-salularidinol spontaneously doses the oxide bridge at pH 8-9 by allylic elimination furnishing the morphine precursor thebaine.

引用

页码：3897 / 3900

页数：4

共 12 条

[1] INVESTIGATIONS ON BIOSYNTHESIS OF MORPHINE ALKALOIDS [J].

BARTON, DHR ;

KIRBY, GW ;

STEGLICH, W ;

THOMAS, GM ;

BATTERSBY, AR ;

DOBSON, TA ;

RAMUZ, H .

JOURNAL OF THE CHEMICAL SOCIETY, 1965, (APR) :2423-+

[2]

BATTERSBY AR, 1963, P CHEM SOC LONDON, P189

[3]

COOPER TG, 1969, J BIOL CHEM, V244, P3507

[4] CLOSURE OF OXIDE BRIDGE IN MORPHINE SERIES [J].

GATES, M ;

SHEPARD, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1962, 84 (21) :4125-&

[5] PURIFICATION AND CHARACTERIZATION OF SALUTARIDINE - NADPH 7-OXIDOREDUCTASE FROM PAPAVER-SOMNIFERUM [J].

GERARDY, R ;

ZENK, MH .

PHYTOCHEMISTRY, 1993, 34 (01) :125-132

[6]

GERARDY R, 1993, PHYTOCHEMISTRY, V32, P79, DOI 10.1016/0031-9422(92)80111-Q

[7] LOCALIZATION OF BETA-OXIDATION ENZYMES IN PEROXISOMES ISOLATED FROM NONFATTY PLANT-TISSUES [J].

GERHARDT, B .

PLANTA, 1983, 159 (03) :238-246

[8] THE TRANSFORMATION OF NEOPINONE TO CODEINONE IN MORPHINE BIOSYNTHESIS PROCEEDS NONENZYMATICALLY [J].

GOLLWITZER, J ;

LENZ, R ;

HAMPP, N ;

ZENK, MH .

TETRAHEDRON LETTERS, 1993, 34 (36) :5703-5706

[9]

JOURNET EP, 1987, METHOD ENZYMOL, V148, P234

[10] REVISION OF THE CONFIGURATION AT C-7 OF SALUTARIDINOL-I, THE NATURAL INTERMEDIATE IN MORPHINE BIOSYNTHESIS [J].

LOTTER, H ;

GOLLWITZER, J ;

ZENK, MH .

TETRAHEDRON LETTERS, 1992, 33 (18) :2443-2446

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