Stereospecific synthesis and characterization of aminoglycoside ligands from diethylenetriamine

被引：20

作者：

Gaucher, SP ^{[1
]}

Pedersen, SF ^{[1
]}

Leary, JA ^{[1
]}

机构：

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1999年 / 64卷 / 11期

关键词：

D O I：

10.1021/jo9900331

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient synthetic route to diglycosylamines derived from diethylenetriamine and D-glucose, D-galactose, D-allose, or L-fucose is presented where the stereochemically pure product is easily isolated and crystallized as a hydrochloride salt. The diglucosyl diethylenetriamine analogue is characterized by X-ray crystallography, and the chloride ion is shown to stabilize the compound in the crystalline state. These ligands provide simple and efficient routes to various diastereomeric metal N-glycoside coordination complexes that are currently being studied by mass spectrometry.

引用

页码：4012 / 4015

页数：4

共 25 条

[1] Amadori M., 1931, ATTI ACCAD NAZ LIN, V13, P72
[2] ASMA MR, 1998, J AM SOC MASS SPECTR, V8, P987
[3] CHAPLIN MF, 1984, CARBOHYDRATE ANAL
[4] FUKUDA M, 1993, GLYCOBIOLOGY
[5] Determining anomericity of the glycosidic bond in Zn(II)-diethylenetriamine-disaccharide complexes using MSn in a quadrupole ion trap
Gaucher, SP
Leary, JA
[J]. JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 1999, 10 (03) : 269 - 272
[6] Stereochemical differentiation of mannose, glucose, galactose, and talose using zinc(II) diethylenetriamine and ESI ion trap mass spectrometry
Gaucher, SP
Leary, JA
[J]. ANALYTICAL CHEMISTRY, 1998, 70 (14) : 3009 - 3014
[7] LINKAGE POSITION DETERMINATION IN LITHIUM-CATIONIZED DISACCHARIDES - TANDEM MASS-SPECTROMETRY AND SEMIEMPIRICAL CALCULATIONS
HOFMEISTER, GE
ZHOU, Z
LEARY, JA
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (16) : 5964 - 5970
[8] REDUCTIVE AMINATION OF ALDOHEXOSES WITH MONOFUNCTIONAL AND BIFUNCTIONAL ALKYL AMINES - CONVERSION OF CARBOHYDRATES INTO EDTA TYPE COMPLEXING AGENTS
LAMMERS, H
PETERS, JA
VANBEKKUM, H
[J]. TETRAHEDRON, 1994, 50 (27) : 8103 - 8116
[9] NEW ASPECTS OF THE MAILLARD REACTION IN FOODS AND IN THE HUMAN-BODY
LEDL, F
SCHLEICHER, E
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1990, 29 (06) : 565 - 594
[10] SYNTHESIS AND HYDROLYSIS OF N,N'-DIGLYCOPYRANOSYLETHYLENEDIAMINES
MACLEOD, JM
[J]. CARBOHYDRATE RESEARCH, 1979, 75 (OCT) : 71 - 81

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