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D-Ribonolactone, A Versatile Synthetic Precursor of Biologically Relevant Scaffolds

[ Vol. 12 , Issue. 5 ]

Author(s):

Gustavo P. Silveira, Herbert M. Cardozo, Thaís A. Rossa and Marcus M. Sá   Pages 584 - 602 ( 19 )

Abstract:


D-Ribonolactone is a carbohydrate derivative of the aldonolactone family which serves as a versatile chiral pool for the total synthesis of natural products such as malayamycin, varitriol, mannostatin, shikimic acid, herbarumins, neplanocins, and many others. Also, the preparation of new C-nucleosides starting from D-ribonolactone has attracted the attention of several groups in the past decade, since this class of molecules is much less amenable to enzymatic and acid-catalyzed hydrolysis than natural and synthetic N-nucleosides. In addition, the extension of the genetic alphabet could produce new combinations of three-letter codons, potentially generating proteins containing nonbiogenic amino acids, resulting in non-natural properties. This review addresses recent methodologies (published in the past two decades) for the preparation of D-ribonolactone and its analogues, as well as their use as building blocks for the synthesis of naturally occurring compounds and biologically relevant entities in the fields of medicinal chemistry and chemical biology.

Keywords:

D-Ribonolactone, C-nucleosides, Heterocycle, Synthesis, Medicinal Chemistry.

Affiliation:

Departamento de Química, Universidade Federal de Santa Catarina, P.O. Box 88040-900, Florianópolis, SC, Brazil.

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