Glycosylamines nucleosides

N-Glycosyl derivatives are conveniently named as glycosylamines. In the case of complex heterocyclic amines, such as nucleosides, the same approach is used. 

Figure 9.13 A glycosylamine. Adenosine is a nucleoside and is an example of a glycosylamine in which the nitrogen atom of the purine, adenine, is linked directly to carbon 1 of /3-D-ribofuranose.

Nucleosides (2) and nucleotides are examples of the latter (glycosylamine) type. 

A test of this hypothesis would lie in studying the products of the reaction of a 2-deoxy analog of LXX with LXVII, LXXI, or LXXIV, in order to ascertain whether the a and /3 anomers of the nucleoside would be formed. Such a 2-deoxyglycosylamine derivative has not yet been synthesized for the present, this effectively precludes the use of the glycosylamine reaction for the synthesis of 2-deoxypentonucleosides. 

Nucleoside Glycosylamine made by attaching a nucleobase to a ribose or deoxyribose ring (for example, cytidine, uridine, adenosine, guanosine, thymidine, and inosine)... 

Nucleosides - Ribosyl or deoxyribosyl derivatives (rarely, other glycosyl derivatives) of certain pyrimidine or purine bases. They are thus glycosylamines or N-glycosides related to nucleotides by the lack of phosphorylation. [5]... 

Extension of Jackson and Hudson s approach is also feasible with 2-keto pyranosides, nucleosides, some types of anhydrides, " nonreducing and reducing disaccharides,and glycosylamines. ... 

Maltosylamine has been prepared crystalline by prolonged exposure of maltose to methanolic ammonia containing ammonium chloride, and it was shown to possess specific inhibitory activity towards sweet potato jS-amylose. Furanoid glycosylamines have been similarly prepared from 5-O-trityl-D-ribose, -D-arabinose, -D-xylose, and -2-deoxy-D-ribose and are potentially useful in the synthesis of nucleosides. ... 

A 27-step synthesis of spicamycin amino-nucleoside (1) from myo-inositol featured a palladium-catalysed coupling of 5-chloropurine and with a glycosylamine derivative. Full details have been published on the products obtained from reactions of 5,6-diamino-2-methoxy-3-methylpyrimidi iV-4(3H)-one with xylose and with other pentoses in alcohol solutions (cf. Vol. 27, p. 127, ref. 8)."... 

The most important derivatives of pyrimidines and purines are nucleosides. Nucleosides are glycosylamines in which a pyrimidine or purine nitrogen is bonded to the anomeric carbon of a carbohydrate. The nucleosides listed in Table 26.2 are the main building blocks of nucleic acids. In RNA the carbohydrate component is D-ribofuranose in DNA it is 2-deoxy-D-ribofuranose. 

Adenosine is an example of a glycosylamine that is also called a nucleoside. 

Nucleosides are glycosylamines in which the amino component is a pyrimidine or a purine (Section 20. IB) and in which the sugar component is either D-ribose or 2-deoxy-D-ribose (i.e., D-ribose minus the oxygen at the 2 position). 

The glycosylamines have been of considerable interest because the nucleosides, hydrolytic products of the nucleic acids, are members of the group. The discovery that several biologically important coenzymes are glycosylamines or their derivatives has greatly stimulated research in the field. 

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