TOTAL SYNTHESIS OF OPTICALLY PURE NUCLEOSIDE-Q - DETERMINATION OF ABSOLUTE-CONFIGURATION OF NATURAL NUCLEOSIDE-Q

被引：57

作者：

OHGI, T ^{[1
]}

KONDO, T ^{[1
]}

GOTO, T ^{[1
]}

机构：

[1] NAGOYA UNIV,DEPT AGR CHEM,NAGOYA,AICHI 464,JAPAN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 13期

关键词：

D O I：

10.1021/ja00507a032

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Two diastereomers of 7-(3,4-trans-4,5-m-4,5-dihydroxycyclopent-1-en-3-ylaminomethyl)-7-deazaguanosine having the β-D-ribosyl group were synthesized, one of which, having the 3S,4R,5S configuration in its cyclopentenyl side chain, was proved to be identical in all respects, including ORD and CD, with natural nucleoside Q, thus determining the absolute and anomeric configurations of the latter. © 1979, American Chemical Society. All rights reserved.

引用

收藏

页码：3629 / 3633

页数：5

相关论文

共 24 条

[1]

ANSAI K, 1957, J ANTIBIOT A, V10, P20

[2] A USEFUL MODEL OF OPTICAL ACTIVITY .3. THE OPTICAL ACTIVITY OF ENDOCYCLIC OLEFINS [J].

BREWSTER, JH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1959, 81 (20) :5493-5500

[3] NUCLEOTIDE SEQUENCE OF ESCHERICHIA COLI TYROSIE TRANSFER RIBONUCLEIC ACID [J].

DOCTOR, BP ;

LOEBEL, JE ;

SODD, MA ;

WINTER, DB .

SCIENCE, 1969, 163 (3868) :693-&

[4]

FARKAS WR, 1973, J BIOL CHEM, V248, P7780

[5] AMBER SUPPRESSION - A NUCLEOTIDE CHANGE IN ANTICODON OF A TYROSINE TRANSFER RNA [J].

GOODMAN, HM ;

ABELSON, J ;

LANDY, A ;

BRENNER, S ;

SMITH, JD .

NATURE, 1968, 217 (5133) :1019-&

[6] POSSIBLE ANTICODON SEQUENCES OF TRANSFER-RNAHIS, TRANSFER-RNAASN, AND TRANSFER-RNAASP FROM ESCHERICHIA-COLI B - UNIVERSAL PRESENCE OF NUCLEOSIDE Q IN FIRST POSITION OF ANTICODONS OF THESE TRANSFER RIBONUCLEIC-ACIDS [J].

HARADA, F ;

NISHIMURA, S .

BIOCHEMISTRY, 1972, 11 (02) :301-+

[7] DISTRIBUTION OF MODIFIED NUCLEOSIDE Q AND ITS DERIVATIVES IN ANIMAL AND PLANT TRANSFER-RNAS [J].

KASAI, H ;

KUCHINO, Y ;

NIHEI, K ;

NISHIMURA, S .

NUCLEIC ACIDS RESEARCH, 1975, 2 (10) :1931-1939

[8] STRUCTURE OF QSTAR NUCLEOSIDE ISOLATED FROM RABBIT LIVER TRANSFER RIBONUCLEIC-ACID [J].

KASAI, H ;

NAKANISHI, K ;

MACFARLANE, RD ;

TORGERSON, DF ;

OHASHI, Z ;

MCCLOSKEY, JA ;

GROSS, HJ ;

NISHIMURA, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (16) :5044-5046

[9] STRUCTURE OF MODIFIED NUCLEOSIDE-Q ISOLATED FROM ESCHERICHIA-COLI TRANSFER RIBONUCLEIC-ACID - 7-(4,5-CIS-DIHYDROXY-1-CYCLOPENTEN-3-YLAMINOMETHYL)-7-DEAZAGUANOSINE [J].

KASAI, H ;

OHASHI, Z ;

HARADA, F ;

NISHIMURA, S ;

OPPENHEIMER, NJ ;

CRAIN, PF ;

LIEHR, JG ;

MINDEN, DLV ;

MCCLOSKEY, JA .

BIOCHEMISTRY, 1975, 14 (19) :4198-4208

[10] SYNTHESIS OF 5-METHYLTUBERCIDIN AND ITS ALPHA-ANOMER VIA CONDENSATION OF ANION OF 4-METHOXY-5-METHYL-2-METHYLITHIOPYRROLO [2,3-D] PYRIMIDINE AND 2, 3, 5-TRI-O-BENZYL-D-RIBOFURANOSYL BROMIDE [J].

KONDO, T ;

OHGI, T ;

GOTO, T .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1977, 41 (08) :1501-1507