Fluorinated carbohydrates, biological

Synthesis and Biological Activities of Compounds Containing Fluorinated Carbohydrates. 186... 

A. B. Foster Synthesis and biological activity of fluorinated carbohydrates... 

Csuk and Glanzer [48] published a detailed compilation of NMR data of fluorinated carbohydrates. Two other reviews on fluoro-sugars also mention chemical characteristics and biological applications [49,50]. 

Fluorinated carbohydrates have recently received much attention because of their importance in the study of the enzyme-carbohydrate interactions and their interesting biological activity [56], Hara et al. [57] achieved the deoxyfluorination of primary and anomeric hydroxyl groups of a series of protected carbohydrates, for example 65 into 66 (70%) (Scheme 12.31, a representative example) and 67 into 68 (90%) (Scheme 12.32, a representative example), with good yields, by use of N,N-diethyl-a,a-difluoro-(m.-methylbenzyl)amme (DFMBA), which has previously proved to be a selective reagent for the synthesis of fluorinated alcohols and carboxylic acids [58], Chemoselective deoxyfluorination at the anomeric position... 

Santi, D V, Pogolotti, A L Jr, Newman, E M, Wataya, T In Biomedia nal Aspects of Fluorine Chemistry, Filler, R, Kobayashi, Y, Eds, Kodan-shaLtd Tokyo, and Elsevier Biomedical Amsterdam, 1982, pp 123-142 Withers, S G, Street, I P,Percival, M D a Fluonnated Carbohydrates Chemical and Biological Aspects, Taylor, N F, Ed, ACS Symposium Senes 374, Amencan Chemical Society Washmgton, DC, 1988, pp 59 77... 

The selective introduction of fluorine is of continuing interest not only because of the synthetic challenge but also because of the possibility of a dramatic change in biological activity. The fluoride-ion displacement of carbohydrate trifluoromethanesulfonates using tris(dimethylamino)sulfonium... 

Building blocks derived from microbial transformations are usually employed as the key units of fluorinated analogs of appropriate natural products or synthetic biologically active materials [42-45]. Among such useful compounds, trifluoromethylated carbohydrates constitute one of the most interesting fields for intensive study. Novel and efficient routes to access a variety of chiral... 

The current review is of necessity selective. Over the two year period covered, there has been impressive advances in several areas of P(V) chemistry. For example, biological aspects of quinquevalent phosphorus acids chemistry continue to increase in importance. A wide variety of natural and unnatural phosphates including inositols, lipids, some carbohydrates and their phospho-nates, phosphinates and fluorinated analogues has been synthesized. Special attention has been paid to the synthesis of phosphorus analogues of all types of amino acids and some peptides. Numerous investigations of phosphate ester hydrolysis and related reactions continue to be reported. Interest in approaches to easier detoxification of insecticides continues. A number of new and improved stereoselective synthetic procedures have been elaborated. The importance of enantioselective and dynamic kinetic asymmetric transformations is illustrated in many publications. 

Up to date, a lots of fluorinated compounds were synthesized and biologically evaluated. Among these fluorinated compounds, fluorinated sugars have recently attracted more and more attentions from organic and medicinal chemists. It should be noted that just one fluorine-containing carbohydrate derivative has been isolated from... 

An extensive series of reviews of fluorinated biological analogues including F-carbohydrates was published in 1972 in the form of a CIBA Symposium volume (1 ) and an ACS Symposium in 1976 ( ). A substemtial, useful source book cataloguing properties of carbohydrate derivatives, including some fluorosugcurs has recently been published by Collins ( ). ... 

The practice of introducing fluorine atoms into molecules of biological interest, such as steroids, carbohydrates, antitumor agents, and other biologi-... 

As part of an issue of Carbohydrate Research devoted to reviewing the whole area of fluorinated sugars, Pankiewicz has discussed nucleosides fluorinated in the sugar moiety, covering both synthesis and biological activity. Another review has also covered recent strategies for the synthesis of fluoronucleosides, with some consideration of structure-activity relationships. ... 

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