Synthesis of pyrrolo[2,3-d]pyrimidines that are structurally related to methylated guanosines from tRNA and the nucleoside Q analogs, PreQ(0) and PreQ(1)

被引:9
作者
Cheng, CS
Hoops, GC
Earl, RA
Townsend, LB
机构
[1] UNIV MICHIGAN,COLL PHARM,DEPT MED CHEM,ANN ARBOR,MI 48109
[2] UNIV MICHIGAN,COLL LITERATURE SCI & ARTS,DEPT CHEM,ANN ARBOR,MI 48109
[3] UNIV UTAH,COLL PHARM,DEPT MED CHEM,SALT LAKE CITY,UT 84112
来源
NUCLEOSIDES & NUCLEOTIDES | 1997年 / 16卷 / 04期
关键词
D O I
10.1080/07328319708001355
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The N-3- and N-2-methylated analogs of several 5-substituted 2-amino-7-(beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidin-4-ones were synthesized from 5-cyano-2,4-dichloro-7-(2,3,5-tri-(O>$) over bar under bar>-acetyl-beta-D-ribofuranosyl)pyrrolo[2,3-d]pyrimidine (10) These compounds are analogs of nucleoside Q that are methylated in a manner similar to some of the naturally occurring methylated guanosines.
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收藏
页码:347 / 364
页数:18
相关论文
共 28 条
[1]  
ADLER M, 1958, J BIOL CHEM, V230, P717
[2]   UAG READTHROUGH DURING TMV RNA TRANSLATION - ISOLATION AND SEQUENCE OF 2 TRANSFER RNASTYR WITH SUPPRESSOR ACTIVITY FROM TOBACCO PLANTS [J].
BEIER, H ;
BARCISZEWSKA, M ;
KRUPP, G ;
MITNACHT, R ;
GROSS, HJ .
EMBO JOURNAL, 1984, 3 (02) :351-356
[3]   WILD-TYPE TRANSFER-RNA GTYR READS THE TMV RNA STOP CODON, BUT Q-BASE-MODIFIED TRANSFER-RNA GTYR DOES NOT [J].
BIENZ, M ;
KUBLI, E .
NATURE, 1981, 294 (5837) :188-190
[4]   SYNTHESIS OF 2-AMINO-5-CYANO-7-(BETA-D-RIBOFURANOSYL)-PYRROLO[2,3-D]PYRIMIDIN-4-ONE- IMPORTANT PRECURSOR FOR SYNTHESIS OF NUCLEOSIDE Q AND QSTAR [J].
CHENG, CS ;
HINSHAW, BC ;
PANZICA, RP ;
TOWNSEND, LB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (24) :7870-7872
[5]  
GREGSON JM, 1993, J BIOL CHEM, V268, P10076
[6]   ABSENCE OF TRANSFER RNA-GUANINE TRANSGLYCOSYLASE IN A HUMAN COLON ADENOCARCINOMA CELL-LINE [J].
GUNDUZ, U ;
ELLIOTT, MS ;
SEUBERT, PH ;
HOUGHTON, JA ;
HOUGHTON, PJ ;
TREWYN, RW ;
KATZE, JR .
BIOCHIMICA ET BIOPHYSICA ACTA, 1992, 1139 (03) :229-238
[8]   CHROMATOGRAPHIC ANALYSIS OF THE AMINOACYL-TRANSFER RNAS WHICH ARE REQUIRED FOR TRANSLATION OF CODONS AT AND AROUND THE RIBOSOMAL FRAMESHIFT SITES OF HIV, HTLV-1, AND BLV [J].
HATFIELD, D ;
FENG, YX ;
LEE, BJ ;
REIN, A ;
LEVIN, JG ;
OROSZLAN, S .
VIROLOGY, 1989, 173 (02) :736-742
[9]   PYRROLOPYRIMIDINE NUCLEOSIDES .10. SYNTHESIS OF CERTAIN 4,5-DISUBSTITUTED 7-(BETA-D-RIBOFURANOSYL)PYRROLO[2,3-D]PYRIMIDINES RELATED TO TOYOCAMYCIN AND SANGIVAMYCIN [J].
HINSHAW, BC ;
LEONOUDAKIS, O ;
SCHRAM, KH ;
TOWNSEND, LB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (13) :1248-1253
[10]  
HJALMARSSON KJ, 1983, J BIOL CHEM, V258, P1343