Synthesis of transition state inhibitors for N-riboside hydrolases and transferases

被引：77

作者：

Furneaux, RH

Limberg, G

Tyler, PC

Schramm, VL

机构：

[1] IND RES LTD,LOWER HUTT,NEW ZEALAND

[2] YESHIVA UNIV ALBERT EINSTEIN COLL MED,DEPT BIOCHEM,BRONX,NY 10461

来源：

TETRAHEDRON | 1997年 / 53卷 / 08期

关键词：

D O I：

10.1016/S0040-4020(96)01172-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of 1,4-dideoxy-1,4-imino-1-(S)-(substituted phenyl)-D-ribitols bearing aromatic OH, NH2, NO2, CO2H and halogeno moieties, and a 3-pyridyl analogue have been synthesized. The key step is the condensation of aryllithium or aryl Grignard reagents with the imine 3; derived from the protected 1,4-dideoxy-1,4-imino-D-ribitol 4. (C) 1997 Elsevier Science Ltd.

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收藏

页码：2915 / 2930

页数：16

相关论文

共 26 条

[1] AMIDRAZONE ANALOGS OF D-RIBOFURANOSE AS TRANSITION-STATE INHIBITORS OF NUCLEOSIDE HYDROLASE [J].

BOUTELLIER, M ;

HORENSTEIN, BA ;

SEMENYAKA, A ;

SCHRAMM, VL ;

GANEM, B .

BIOCHEMISTRY, 1994, 33 (13) :3994-4000

[2]

BOUTELLIER M, 1995, SYNLETT, P510

[3] Inhibition of ricin by an RNA stem-loop containing a ribo-oxocarbenium mimic [J].

Chen, XY ;

Link, TM ;

Schramm, VL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (12) :3067-3068

[4] PARTIAL-PURIFICATION AND PROPERTIES OF A NUCLEOSIDE HYDROLASE FROM CRITHIDIA [J].

DEWEY, VC ;

KIDDER, GW .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1973, 157 (02) :380-387

[5]

ENDO Y, 1987, J BIOL CHEM, V262, P8128

[6]

ESTUPINAN B, 1994, J BIOL CHEM, V269, P23068

[7] POLYHYDROXYLATED PYRROLIDINES FROM SUGAR LACTONES - SYNTHESIS OF 1,4-DIDEOXY-1,4-IMINO-D-GLUCITOL FROM D-GALACTONOLACTONE AND SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-ALLITOL, 1,4-DIDEOXY-1,4-IMINO-D-RIBITOL, AND (2S,3R,4S)-3,4-DIHYDROXYPROLINE FROM D-GULONOLACTONE [J].

FLEET, GWJ ;

SON, JC .

TETRAHEDRON, 1988, 44 (09) :2637-2647

[8] Inosine-uridine nucleoside hydrolase from Crithidia fasciculata. Genetic characterization, crystallization, and identification of histidine 241 as a catalytic site residue [J].

Gopaul, DN ;

Meyer, SL ;

Degano, M ;

Sacchettini, JC ;

Schramm, VL .

BIOCHEMISTRY, 1996, 35 (19) :5963-5970

[9] PURINE AND PYRIMIDINE METABOLISM IN THE TRYPANOSOMATIDAE [J].

HAMMOND, DJ ;

GUTTERIDGE, WE .

MOLECULAR AND BIOCHEMICAL PARASITOLOGY, 1984, 13 (03) :243-261

[10] CORRELATION OF THE MOLECULAR ELECTROSTATIC POTENTIAL SURFACE OF AN ENZYMATIC TRANSITION-STATE WITH NOVEL TRANSITION-STATE INHIBITORS [J].

HORENSTEIN, BA ;

SCHRAMM, VL .

BIOCHEMISTRY, 1993, 32 (38) :9917-9925