Fluorosulfonylbenzoyl Nucleosides

In several cases, reaction of 5 -FSBA with cysteine has been postulated to involve initial formation of a thiolsulfonate derivative of 5 -FSBA, followed by 

In many cases, 5 -FSBA reacts at active sites however, in bovine liver glutamate dehydrogenase, all the fluorosulfonylbenzoyl nucleosides react at regulatory sites. This enzyme is a hexamer of identical subunits, each of which has two regulatory sites for ADP, two for GTP, and two for NADH (one catalytic 

Epidermal growth factor-.stimulated protein kinase 149- 152 

Other ATP/ADP and Adenosine Binding Proteins Covalently Labeled by 5 -p-Fluorosulfonylbenzoyladenosine 

The compound 5 -p-fluorosulfonylbenzoylinosine (5 -FSBl) was first described by Williamson and Meister (769). This compound has been found to react with 5-oxo-L-prolinase (769) and with bovine heart mitochondrial Fr ATPase (796), both of which can bind ITP. Furthermore, the synthesis of several new S -p-fluorosulfonylbenzoylarabinosyl nucleoside analogs has recently been reported (797) these include 5 -FSB derivatives of arabinosylcytosine, arabino-syladenine, arabinosylguanine, arabinosyiuracil, and thymidine. 

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As a class of site-directed modifying agents, the fluorosulfonylbenzoyl nucleosides offer several favorable features they are structurally related to nucleotides, even though they lack phosphoryl groups and require the addition of a small... 

Difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-pentanoic acid 4,ll-bis[(2-Aminoethyl)amino]anthra[2,3-b]furan-5,10-diones 4(l-Anilino-podophyllotoxin derivatives 5-Aza-2 -deoxycytidine 5-Bromotetrandrine 5-Cyclohexylindolyl-2 -deoxyribose (non-natural nucleoside) 5 -Fluorosulfonylbenzoyl 5 -adenosine 5-Fluorouracil 5,5-Diphenylbarbituric acid 6-[(2S,4R,6E)-4-Methyl-2-(methylamino)-3-oxo-6-octenoic acid] cyclosporine D (PSC833) 6-Hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid 6-Mercaptopurine 6-Prenylchrysin 6-Thioguanine 6,7-Dimethoxy-... 

Fig. S. Ruorosulfonylbenzoyl nucleoside affinity labels, (a) S -/7-Ruorosulfonylbenzoyladeno-sine (b) S -p-fluorosulfonylbenzoylguanosine (c) S -p-Ruorosulfonylbenzoyl-I.N -ethenoadeno-sine and (d) S -p-fluorosulfonylbenzoyl-8-azidoadenosine.

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