Circular dichroism and the anomeric configuration of C-glycofuranosyl-2-phenyl-2H-1,2,3-triazoles

被引：6

作者：

Sallam, MAE ^{[1
]}

机构：

[1] Univ Alexandria, Fac Sci, Dept Chem, Alexandria, Egypt

来源：

ENANTIOMER | 2002年 / 7卷 / 06期

关键词：

anomeric configuration; circular dichroism; Cotton effect; C-nucleosides; 1,2,3-triazoles;

D O I：

10.1080/10242430215712

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：

Circular dichroism spectra of a series of 4-(tetra-hydroxy-tetryl-1-yl)-2-phenyl-2H-1,2,3-triazoles were measured and the sign of their Cotton effects was correlated to the absolute configuration of the hydroxyl. group a to the triazole base moiety. Those having the D-glycero-configuration in their Fischer projection formula show positive Cotton effect and those with the L-glycero-configuration show negative Cotton effect. This correlation was extended for the assignment of the anomeric configuration of the corresponding glycofuranosyl-C-nucleosides.

引用

页码：283 / 286

页数：4

共 13 条

[1]

ELKHADEM H, 1963, TETRAHEDRON LETT, P1887

[2]

ELKHADEM H, 1963, J ORG CHEM, V28, P2478

[3] THE ACTION OF COPPER SULFATE ON THE PHENYL OSAZONES OF THE SUGARS .2. SOME NEW OSOTRIAZOLES [J].

HASKINS, WT ;

HANN, RM ;

HUDSON, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1945, 67 (06) :939-941

[4] The significance of certain numerical relations in the sugar group [J].

Hudson, CS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1909, 31 :66-86

[5] ROTATORY DISPERSION STUDIES .6. PHENYLOSOTRIAZOLE DERIVATIVES OF ALDO SUGAR FAMILY [J].

LYLE, GG ;

PIAZZA, MJ .

JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (06) :2478-&

[6] PHENYLOSOTRIAZOLE RULE FOR DETERMINING CONFIGURATION OF SUGARS [J].

MILLS, JA .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1964, 17 (02) :277-&

[7] CORRELATION BETWEEN THE CIRCULAR-DICHROISM SPECTRA OF C-NUCLEOSIDE 1,2,3-OSOTRIAZOLE ANALOGS AND THEIR ANOMERIC CONFIGURATION [J].

SALLAM, MAE .

CARBOHYDRATE RESEARCH, 1984, 129 (JUL) :33-41

[8] Acid-catalyzed dehydrative cyclization of 4-(D-galacto-pentitol-1-yl)-2-phenyl-2H-1,2,3-triazole.: Synthesis and anomeric configuration of D-lyxo-C-nucleoside analogs [J].

Sallam, MAE ;

Megid, SMEA ;

Townsend, LB .

CARBOHYDRATE RESEARCH, 2001, 330 (01) :53-63

[9] Studies on epimeric-D-arabino- and -D-ribo-tetritol-1-yl-2-phenyl-2H-1,2,3-triazoles.: Synthesis and anomeric configuration of 4-(α- and β-D-erythrofuranosyl)-2-phenyl-2H-1,2,3-triazole C-nucleoside analogs [J].

Sallam, MAE ;

Louis, FF ;

Cassady, JM .

NUCLEOSIDES & NUCLEOTIDES, 1998, 17 (04) :769-783

[10] STUDIES ON ANHYDRO-OSAZONES .2. STRUCTURE AND ANOMERIC CONFIGURATION OF THE 3,6-ANHYDRO-OSAZONE DERIVATIVES OBTAINED FROM D-LYXO-HEXULOSE PHENYL-OSAZONE AND D-XYLO-HEXULOSE PHENYLOSAZONE [J].

SALLAM, MAE ;

HEGAZY, EIA .

CARBOHYDRATE RESEARCH, 1981, 90 (01) :91-98

← 1 2 →