P-thioglucosides

Access to P-mannosides [209] is illustrated by the preparation of 179 from P-glucoside 178 by oxidation of the equatorial 2-OH followed by stereoselective reduction to give the axial alcohol an efficient indirect route to the a-mannosides [206] utilizes the P-thioglucoside 182, readily obtained from epoxide 173, proceeding via an oxidation-reduction protection sequence to give P-thiomannoside glycosyl donor 184, from which a-mannoside 185 can be stereoselectively prepared. 

Although cytochrome c oxidase from S. novella is cytochrome aa3-type, its molecular features are very unique (Shoji et al., 1992). In general, cytochrome aa3-type oxidase has two heme A molecules and 2-3 copper atoms in the minimal structural unit, while the S. novella oxidase has one heme A molecule and one copper atom in the minimal structural unit constituted of two subunits (32 and 23 kDa). The oxidase occurs as the monomer of the minimal structural unit in the solution containing 0.5% n-octyl-D-P-thioglucoside (OTG). The monomer catalyzes the rapid oxidation of ferrocytochrome c, its heme A molecule reacts completely with carbon monoxide (CO) under 100% carbon monoxide atmosphere, and its copper shows a big signal at g = 2.01 in EPR spectrum the monomer seems to be a cytochrome a3 having Cua (Shoji et al., 1992). 

For an example of glycoside synthesis with 0-benzylated 2-benzothiazolyl-1-thio-D-gluco-pyranoside in the presence of Cu(OTf)2, see T. Mukaiyama, T. Nakatsuka, and S. Shoda, An efficient glucosylation of alcohol using 1-thioglucoside derivative, Chem. Lett. p. 87 (1979),... 

Activation of thioglucosides. Thioglucosides are useful for glycosidation since they are more reactive than glycosyl halides. They are known to be activated by methyl triflate, but this triflate is a potent carcinogen. Methylsulfenyl trifluoromethanesulfonate (1) is also an activator and has the advantage that it can be prepared in situ. Thus the 1-thio-p-D-glucopyranoside (p—2) couples with a-D-... 

HUSEBYE, H., CHADCHAWAN, S., WINGE, P., THANGSTAD, O.P., BONES, A.M., Guard cell- and phloem idioblast-specific expression of thioglucoside glucohydrolase 1 (myrosinase) in Arabidopsis., Plant Physiol., 2002,128,1180-1188. 

Thangstad, O.P., Winge, R, Husebye, H. and Bones, A. (1993) The thioglucoside glucohydrolase (myrosinase) gene family in Brassicaceae. Plant Mol Biol, 23, 511-24. 

OTG (n-Octyl-P-D-thioglucoside) HPMC (hydroxipropylmethylcelulose) PG (propylene glycol) PBS (phosphate buffer solution) ICAM-1 (intercellular adhesion molecule-1). ... 

Ogiso, T, Paku, T., Iwaki, M., and Tanino, T. (1994). Mechanism of the enhancement effect of n-octyl-P-rf-thioglucoside on the transdermal penetration of fluorescein isothiocyanate-labeled dextrans and the molecular weight dependence of water-soluble penetrants through stripped skin. Journal of Pharmaceutical Sciences, 83 1676-1681. 

Franck et al. [109] suggested a strategy for the synthesis of C-glycosyl benzaldehyde derivatives to be used in porphyrin preparations. They started by condensing 2,3,4,6-tetra-0-acetyl-l-thio-j6-D-glucopyranose with a,a -dibromo-p-xylene to afford thioglucoside 159 (Scheme 29). The latter, by... 

Thiophenols react similarly to phenols 4-methoxythiophenol yielding 70% of a 43 57 a-D/P-D mixture of thioglucosides [32],... 

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