Synthesis of methyl glycoside derivatives of tri- and penta-saccharides related to the antithrombin III-binding sequence of heparin, employing cellobiose as a key starting-material

1988 ◽  
Vol 172 (1) ◽  
pp. 37-64 ◽  
Author(s):  
Yoshitaka Ichikawa ◽  
Ryuji Monden ◽  
Hiroyoshi Kuzuhara
Keyword(s):  
Antithrombin Iii ◽  
Starting Material ◽  
Methyl Glycoside ◽  
Binding Sequence ◽  
Derivatives Of

SYNTHESIS OF 1,1,1-TRICHLORO-2,2-BIS-(p-CYANOPHENYL)-ETHANE

1952 ◽  
Vol 30 (3) ◽  
pp. 203-207 ◽  
Author(s):  
Yvon Perron ◽  
Roger Barré
Keyword(s):  
Condensation Product ◽  
Starting Material ◽  
Derivatives Of

The synthesis of 1,1,1-trichloro-2,2-bis-(p-cyanophenyl)-ethane was carried out with the condensation product of chloral and toluene as starting material. This product was converted, through the corresponding tetraacetate, to 1,1,1-trichloro-2,2-bis-(p-aldehydophenyl)-ethane which in turn reacted with hydroxylamine to give the dioxime. The subsequent dehydration of the latter gave rise to the desired dinitrile. The corresponding dichloro derivatives of the oxime and nitrile were also prepared.

scholarly journals Antimonial analogues of the acridine series. Dilhydrostibacridines

1933 ◽  
Vol 143 (848) ◽  
pp. 38-47 ◽  
Keyword(s):  
Nitro Derivative ◽  
Starting Material ◽  
Arsenic Compounds ◽  
Ring Systems ◽  
Nitrogen Ring ◽  
Derivatives Of

In pursuing our investigation out the antimony analogues of certain nitrogen ring-systems, we Lave now succeeded in obtaining derivatives of dilhydrostibacridines, of when some of the corresponding arsenic compounds have been studied recently by Gump and Stolzenburg. The starting material for the work was o -aminodiphenylmethane obtained from the corresponding nitro derivative when, in turn, was prepared from o -nitrobenzyl chloride and benzene by Taneseseu's modification of the Friedel-Crafts reaction.

scholarly journals The structure of heparin oligosaccharide fragments with high anti-(factor Xa) activity containing the minimal antithrombin III-binding sequence Chemical and13C nuclear-magnetic-resonance studies

1981 ◽  
Vol 197 (3) ◽  
pp. 599-609 ◽  
Author(s):  
B Casu ◽  
P Oreste ◽  
G Torri ◽  
G Zoppetti ◽  
J Choay ◽  
...  
Keyword(s):  
Uronic Acid ◽  
Antithrombin Iii ◽  
Factor Xa ◽  
Amino Sugar ◽  
Active Species ◽  
Model Compounds ◽  
High Affinity ◽  
The Common ◽  
Binding Sequence ◽  
Heparin Oligosaccharides

The chemical composition and the 13C n.m.r. spectra of heparin oligosaccharides (essentially octasaccharides), having high affinity for antithrombin III and high anti-(Factor Xa) activity, prepared by three independent approaches (extraction, partial deaminative cleavage with HNO2 and partial depolymerization with bacterial heparinase), leading to different terminal residues, have been studied and compared with those of the corresponding inactive species. Combined wit chemical data, the spectra of the active oligosaccharides and of their fragmentation products afforded information on composition and sequence. The three types of active oligosaccharides were shown to have the common hexasaccharide core I-Aa-G-As*-Is-As, where I and alpha-L-idopyranosyl-uronic acid, Aa = 2-acetamido-2-deoxy-alpha-D-glucopyranose, G = beta-D-glucopyranosyl-uronic acid, Is = alpha-L-idopyranosyluronic acid 2-O-sulphate, As = 2-deoxy-2-sulphamino-alpha-D-glucopyranose 6-O-sulphate. The fourth residue (As*) is an unusually substituted amino sugar resistant to mild deamination. The 13C spectra of the active species are characterized by signals from the above atypical amino sugar, the most evident of which is at 57.7 p.p.m. These signals, compared with those of appropriate synthetic model compounds, are compatible with the recently proposed 3-O-sulphation of the residue As* [Lindahl, Bäckström, Thunberg & Leder (1980) Proc. Natl. Acad. Sci. U.S.A. 77, 6551-6555].

A COMPARISON OF THE BINDING OF ANTITHROMBIN III AND HEPARIN COFACTOR II TO HEPARINS, NATURALLY OCCURRING GLYCOSAMINOGLYCANS AND OTHER SULPHATED POLYMERS

1987 ◽  
Author(s):  
J Dawes ◽  
D S Pepper
Keyword(s):  
Molecular Weight ◽  
Chain Length ◽  
Antithrombin Iii ◽  
Molar Ratio ◽  
Heparin Binding ◽  
Dextran Sulphate ◽  
Heparin Cofactor Ii ◽  
Wide Range ◽  
Pentosan Polysulphate ◽  
Binding Sequence

Antithrombin III (ATIII) and heparin cofactor II (HCII) are currently thought to be the most important protein mediators of the anticoagulant and antithrombotic activities of glycosamino-glycans. A simple, quantitative method for assessing the affinity of a protein for a sulphated polymer in the liquid phase, based on competition with immobilised heparin, has been developed. Using this technique, the binding of ATIII and HCII to a wide range of glycosaminoglycans and other sulphated polymers have been compared, and the contributions to binding of size, degree of sulphation and backbone structure of the polymers analysed.In the presence of the high protein concentrations found in plasma, unfractionated heparin inhibited the binding of ATIII to immobilised heparin with a Ki of 1 x 10-6. Binding was destroyed by N-desulphation. 1 Results with a range of low molecular weight (LMW) heparins and heparan sulphates are consistent with the view that they all contain the ATIII-binding sequence, but at a lower molar ratio than heparin. Highly sulphated synthetic polymers such as dextran sulphate bound ATIII by a different mechanism, which was molecular weight-dependent.The affinity of HCII for heparins increased markedly with heparin chain length. Binding was largely, but not entirely, mediated by sulphate residues. HCII bound to heparan and dermatan sulphates with lower affinities than to heparin, and to synthetic sulphated polymers with similar or higher affinities. Pentosan polysulphate (SP54) bound HCII as effectively as did heparin. Binding of HCII to dextran sulphate was highly dependent on molecular weight. The affinity of HCII for a sulphated polymer appears to depend both on its chain length and density of sulphation.Thus the profiles of binding of ATIII and HCII to glycosaminoglycans and other sulphated polymers are quite different. This technique is useful both for investigating the interactions of existing therapeutic anticoagulants and assessing new products.

THE SYNTHESIS OF C-9 MODIFIED DERIVATIVES OF THE α-METHYL GLYCOSIDE OF KDN METHYL ESTER

2001 ◽  
Vol 20 (2) ◽  
pp. 227-238 ◽  
Author(s):  
Adele K. Norton ◽  
Gaik B. Kok ◽  
Mark von Itzstein
Keyword(s):  
Methyl Ester ◽  
Methyl Glycoside ◽  
Derivatives Of

Sialic acids in permethylation analysis: preperation and identification of partially O-methylated derivatives of methlyl N-acetyl-N-methyl-β-D-neuraminate methyl glycoside

1978 ◽  
Vol 60 (1) ◽  
pp. 51-62 ◽  
Author(s):  
Herman Van Halbeek ◽  
Johan Haverkamp ◽  
Johannis P. Kamerling ◽  
Johannes F.G. Vliegenthart ◽  
Cornelis Versluis ◽  
...  
Keyword(s):  
Sialic Acids ◽  
Methyl Glycoside ◽  
Derivatives Of

scholarly journals Disodium 5-Cyanoisothiazoledithiolate as a Starting Material for Preparation of New Conductive Solids

1987 ◽  
Vol 42 (8) ◽  
pp. 1050-1051 ◽  
Author(s):  
G. C. Papavassiliou ◽  
G. A. Mousdis ◽  
V. Gionis ◽  
J. S. Zambounis ◽  
S. Y. Yiannopoulos
Keyword(s):  
Cation Radical ◽  
Starting Material ◽  
Derivatives Of

AbstractStarting from disodium 5-cyanoisothiazoledithiolate som e new substituted derivatives of the tetrathiafulvalene and some metal 1,2-dithiolenes with at least an isothiazolo-ring have been prepared. From these com pounds a number of conductive cation radical salts have been obtained.

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