Glucosyl isothiocyanate

Shulman and coworkers showed that ) -D-glucosyl isothiocyanate (43) can be used for the specific inactivation of ) -D-glucosidase B from sweet... 

The synthesis of the bromodeoxy and epoxy analogues of trehazoline were achieved by reaction of the aminobromocyclopentitol 280 with glucosyl isothiocyanate 7 to give the thiourea 427 in 50% yield, which underwent cyclization by the action of yellow HgO to afford aminooxazoline 428 in 60% yield. The trans-bxomo-hydrin 428 was stirred in a suspension of potassium carbonate in methanol to form the epoxide 429 in 81% yield (Scheme 60).109... 

A variation for grafting of sugar units on aminopolysiloxanes has been described, by using an acetyl-protected glucosyl isothiocyanate as the electrophilic carbohydrate reagent, followed by a deprotection step [39]. The aminopropylpolysi-loxane is prepared by redistribution of aminopropyl-D with decamethyltetrasiloxane,... 

Ogura, H. Takeda, K. Takayanagi, H., A Reconfirmation of the Reaction of Glucosyl Isothiocyanate with 2-Chloroethylamine Heterocycles 1989,29,1171. 

Glucosone, 3-deoxy-o-, 75 Glucosylamine, D-, 225 Glucosyl isocyanate, D-, tetraacetate, 220 Glucosyl isothiocyanate, D-, tetraacetate, 220... 

Glucosylamino-2-thiazolines (328) are prepared by the reaction of glucosyl isothiocyanates with 2-chloroethylamine hydrochloride (Equation (59)) <92T6413>. 

Nucleophilic addition of diethyl malonate derivatives 68 to the glucosyl isothiocyanate 58 in the presence of sodium hydride afforded the corresponding A-thioacylglucosylamines 69 in 40-60% yields.170 Adducts incor-porting an a-phenacyl substituent (68, R Ar) were further cyclodehy-drated using phosphoric acid and acetic anhydride to give JV-nucleoside derivatives of 2-pyrroline 70. Under identical reaction conditions, the a-acetonyl derivative (68, R Me) led to the tetrahydropyridine helerocycle 71 (Scheme 21). 

The same group prepared N-(/S-D-glucopyranosyl)oxazolidine-2,4-diones [146] and N-(/l-D-glucopyranosyl)imidazolidine-2,4-diones [147] by desulfurization-condensation of glucosyl isothiocyanate with a-hydroxyacids and J -substituted a-aminoacids, respectively, in the presence of silver triflu-oroacetate and triethylamine. 4-Glucosyl-l,2,4-oxadiazolidine-5-thiones were also prepared by reaction of protected glucosyl isothiocyanates with an ox-aziridine ring [148]. 

Isothiocyanate derivatives of stilbene sulfonates have been utilized with marked success as affinity labels for an anion transport protein of the erythrocyte membrane by Rothstein and his associates, - and glucosyl isothiocyanate has been employed to label a glucose transport protein of the human erythrocyte membrane. Both proteins fall in the 90,000-100,000 dalton range (band 3 in the terminology of Fairbanks et oZ. ). In both cases, transport has been reconstituted using phospholipid vesicles and a band 3 preparation - after aflBnity labeling with the appropriate isothiocyanate had provided preliminary evidence that this protein class might be involved in transport. 

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