19186-40-4Relevant articles and documents
Convenient synthesis of D-talose from D-galactose
Xiao, Hualing,Wang, Guangfa,Wang, Peng,Li, Yingxia
, p. 1229 - 1232 (2010)
The rare and expensive D-talose was conveniently synthesized from readily available D-galactose in four steps with an overall yield of 58%. The key step was the inversion of equatorial 2-OH of galactose to the axial one by S N2 reaction under the modified Lattrell-Dax reaction conditions.
SYNTHESIS AND USE OF GLYCODENDRIMER REAGENTS
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Page/Page column 25; sheet 8, (2010/11/08)
The present invention relates to a chemically modified mutant protein including a cysteine residue substituted for a residue other than cysteine n a precursor protein, the substituted cysteine residue being subsequently modified by reacting the cysteine residue with a glycosylated thiosulfonate. Also a method of producing the chemically modified mutant protein is provided. The present invention also relates to a glycosylated methanethiosulfonate. Another aspect of the present invention is a method of modifying the functional characteristics of a protein including providing a protein and reacting the protein with a glycosylated methanethiosulfonate reagent under conditions effective to produce a glycoprotein with altered functional characteristics as compared to the protein. In addition, the present invention relates to methods of determining the structure-function relationships of chemically modified mutant proteins. The present invention also relates to synthetic methods for producing thio-glycoses, the thio-glycoses so produced, and to methods for producing glycodendrimer reagents.
Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars: L-Gulose, L-Idose, and the Disaccharide Subunit of Bleomycin A2
Dondoni, Alessandro,Marra, Alberto,Massi, Alessandro
, p. 6261 - 6267 (2007/10/03)
The well established one-carbon homologation method of protected monosaccharides employing 2-(trimethylsilyl)thiazole (2-TST) as a formyl anion equivalent has been used for high yield and multigram scale synthesis of the title rare hexoses from L-xylose. Thus, L-gulose has been obtained by stereoselective anti-addition of 2-TST to aldehydo-L-xylose diacetonide followed by thiazole to formyl conversion of the resulting alcohol. The inversion of configuration at C-1 of this alcohol by an oxidation - reduction sequence prior to the aldehyde releasing from thiazole led to L-idose. The same alcohol was readily elaborated into 1,3,4,6-tetra-O-acetyl-L-gulopyranose whose highly stereoselective glycosidation coupling with 3-O-carbamoyl-2,4,6-tri-O-acetyl-α-D-mannosyl diethyl phosphate afforded the same peracetylated disaccharide subunit employed by Boger and Honda in the total synthesis of the antibiotic bleomycin A2.