Carbasugars biology

Lundt I (2003) Iminosugars, isoiminosugars, and carbasugars from activated carbohydrate lactones efficient synthesis of biologically important compounds. In Witzak ZJ, Tatsuta K (eds) Carbohydrate synthons in natural products chemistry synthesis, functionalization and applications. ACS Symposium Series, vol 841. American Chemical Society, Washington, DC,pp 117-140... 

Iminosugars, Isoiminosugars, and Carbasugars from Activated Carbohydrate Lactones Efficient Synthesis of Biologically Important Compounds... 

Because of their large amount of chemically different functionalization, trans-CHD are promising precursors especially for the synthesis of, e.g., carbasugars and their analogs with potential biological activity. The simple, but highly functionalized structure of trans-CHD also has a high potential for diversity-oriented syntheses that could lead to a vast variety of different structures in short chemical reaction sequences. 

In the three major sections of this article, the most representative syntheses of the carbasugars and their closest analogues are analyzed, and the key carbocycle forming manoeuvres are focused on in particular detail. Reference to the observed biological activity is also included, where sufficient data is available. Only recent literature from the 90s onwards was considered, although the most pioneer works on this matter have also been remembered. 

It was then postulated and soon recognised that carbasugars, by virtue of their close resemblance to parent monosaccharides, could possess interesting biological activities. Therefore, after McCasland s pioneering work, there has been extreme interest in the synthesis of carbasugars and, in particular, of carbapyranoid motifs. 

In this chapter we review recent achievements in the chemical synthesis of pyranoid carbasugars, pointing out relevant biological implications where claimed. 

This last section groups together a number of contributions in the field of carbasugar synthesis which, for reasons of space, could not be dealt with in detail in various sections of the text. For the readers comfort, the publications have been sorted into two tables Table 1 lists reviews and accounts about chemistry and biology of carbasugars and Table 2 enumerates recent reaserch papers focusing on the synthesis of variously-sized carbocyclic carbasugars. 

Table 2. Recent Research Articles Dealing with Synthesis and Biology of Carbasugars and Their Analogues...

This class of compounds needs special interest. Such derivatives are especially important, since they serve as extremely useful intermediates in the preparation of a wide variety of carbocyclic compounds with strong biological activity (e. g. inositols, carbasugars, etc.) [5,62]. 

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