Synthesis of rationally designed mechanism-based inactivators of the (S)-adenosyl-L-methionine: Delta(24(25))-sterol methyl transferase

被引：8

作者：

Jia, ZH ^{[1
]}

Zhou, W ^{[1
]}

Guo, D ^{[1
]}

Nes, WD ^{[1
]}

机构：

[1] TEXAS TECH UNIV,DEPT CHEM & BIOCHEM,LUBBOCK,TX 79409

来源：

SYNTHETIC COMMUNICATIONS | 1996年 / 26卷 / 20期

关键词：

D O I：

10.1080/00397919608003800

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of 26,27-cyclopropylidine side chain modified sterols were prepared for the first time from the known aldehydes by Wittig olefination with the ylide from cyclopropyltriphenylphosphonium bromide in butyllithium. Two novel by-products were detected; sterols with nine carbon side chains which lack the terminal isopropyl group and with double bonds in positions 23,24 or 24,25. The structures of the compounds were confirmed by a combination of chromatographic (GLC and HPLC) and spectral (IR, H-1, C-13-NMR) methods.

引用

页码：3841 / 3848

页数：8

共 24 条

[1] SYNTHESIS OF A RATIONALLY DESIGNED INHIBITOR OF THE (S)-ADENOSYL-L-METHIONINE - DELTA-24(25)-STEROL METHYL TRANSFERASE
GUO, DA
NES, WD
SYNTHETIC COMMUNICATIONS, 1995, 25 (17) : 2623 - 2630
[2] STRUCTURAL REQUIREMENTS FOR TRANSFORMATION OF SUBSTRATES BY THE (S)-ADENOSYL-L-METHIONINE - DELTA-24(25)-STEROL METHYL TRANSFERASE
NES, WD
JANSSEN, GG
BERGENSTRAHLE, A
JOURNAL OF BIOLOGICAL CHEMISTRY, 1991, 266 (23) : 15202 - 15212
[3] Mechanism and structural requirements for transformation of substrates by the (S)-adenosyl-L-methionine: Delta(24(25))-sterol methyl transferase from Saccharomyces cerevisiae
Venkatramesh, M
Guo, DA
Jia, ZH
Nes, WD
BIOCHIMICA ET BIOPHYSICA ACTA-LIPIDS AND LIPID METABOLISM, 1996, 1299 (03): : 313 - 324
[4] Substrate-based inhibitors of the (S)-adenosyl-L-methionine:Delta(24(25))- to Delta(24(28))-sterol methyl transferase from Saccharomyces cerevisiae
Nes, WD
Guo, DA
Zhou, W
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1997, 342 (01) : 68 - 81
[5] Substrate-Based Inhibitors of the (S)-Adenosyl-L-Methionine:cap delta24(25)- to cap delta 24(28)-Sterol Methyl Transferase from Saccharomyces cerevisiae
Nes, W. D.
Guo, D.-A.
Zhou, W.
Archives of Biochemistry and Biophysics, 342 (01):
[6] MECHANISM-BASED INHIBITORS OF S-ADENOSYL METHIONINE - DELTA-24-STEROL METHLYTRANSFERASE
SCHMIDT, SJ
ATOR, MA
ADAMS, JL
DOLLE, RE
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 198 : 101 - MEDI
[7] Overexpression, purification, and stereochemical studies of the recombinant (S)-adenosyl-L-methionine:: Δ24(25)- to Δ24(28)-sterol methyl transferase enzyme from Saccharomyces cerevisiae
Nes, WD
McCourt, BS
Zhou, WX
Ma, JZ
Marshall, JA
Peek, LA
Brennan, M
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1998, 353 (02) : 297 - 311
[8] Mechanism of a Class C Radical S-Adenosyl-L-methionine Thiazole Methyl Transferase
Zhang, Zhengan
Mahanta, Nilkamal
Hudson, Graham A.
Mitchell, Douglas A.
van der Donk, Wilfred A.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (51) : 18623 - 18631
[9] The Pneumocystis carinii drug target S-adenosyl-L-methionine:sterol C-24 methyl transferase has a unique substrate preference
Kaneshiro, ES
Rosenfeld, JA
Basselin-Eiweida, M
Stringer, JR
Keely, SP
Smulian, AG
Giner, JL
MOLECULAR MICROBIOLOGY, 2002, 44 (04) : 989 - 999
[10] 24-METHYL-25-AZACYCLOARTANOL, AN ANALOG OF A CARBONIUM-ION HIGH-ENERGY INTERMEDIATE, IS A POTENT INHIBITOR OF (S)-ADENOSYL-L-METHIONINE - STEROL C-24-METHYLTRANSFERASE IN HIGHER-PLANT CELLS
NARULA, AS
RAHIER, A
BENVENISTE, P
SCHUBER, F
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (09) : 2408 - 2409

← 1 2 3 →