Carbohydrates as a chiral pool in organic synthesis: applications in asymmetric catalysis and synthesis of glycopeptides with potential biological activity

• Grant number: 07/02382-7
• Support Opportunities: Regular Research Grants
• Start date: August 01, 2007
• End date: July 31, 2009
• Field of knowledge: Physical Sciences and Mathematics - Chemistry - Organic Chemistry
• Principal Investigator: Diogo Seibert Lüdtke
• Grantee: Diogo Seibert Lüdtke
• Host Institution: Faculdade de Ciências Farmacêuticas (FCF). Universidade de São Paulo (USP). São Paulo , SP, Brazil

Abstract

The present reseach project is centered in the use of carbohydrates, namely D-glucosamine and D-xylose, as a chiral pool for the synthesis of chiral catalysts and ligand with potential application as chiral transfer agents in several enantioselective transformations using organometallic reagents. Moreover, the development of carbohydrate-based chiral organocatalysts that can act in metal-free asymmetric transformations, is also planned.On the other hand, we intend to prepare a series of selenium-containing glycosides and to incorporate them in a number of molecules, such as amino acids, peptides and their derivatives in order to prepare glycopeptides and glycopeptidemimetics. These compounds show a promising profile for a number of significant biological activities and this project should result in several collaborations with other research groups, specially those involved in the fields of biochemistry and toxicology. (AU)

Scientific publications

(6)

(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)

BRAGA, HUGO C.; STEFANI, HELIO A.; PAIXAO, MARCIO W.; SANTOS, FRANCIELLI W.; LUEDTKE, DIOGO S.. Synthesis of 5 `-seleno-xylofuranosides. Tetrahedron, v. 66, n. 19, p. 3441-3446, MAY 8 2010. (07/02382-7)

STEFANI, HELIO A.; VIEIRA, ADRIANO S.; AMARAL, MONICA F. Z. J.; COOPER, LEORA. Synthesis of 5-alkynyl-2,2,6-trimethyl-1,3-dioxin-4-ones and 1,4-disubstituted-1,2,3-triazoles. Tetrahedron Letters, v. 52, n. 33, p. 4256-4261, 2011. (07/02382-7)

VIEIRA, ADRIANO S.; CUNHA, RODRIGO L. O. R.; KLITZKE, CLECIO F.; ZUKERMAN-SCHPECTOR, JULIO; STEFANI, HELIO A.. Highly efficient palladium-catalyzed Suzuki-Miyaura reactions of potassium aryltrifluoroborates with 5-iodo-1,3-dioxin-4-ones in water: an approach to alpha-aryl-beta-ketoesters. Tetrahedron, v. 66, n. 3, p. 773-779, 2010. (07/02382-7)

SCHWAB‚ R.S.; GALETTO‚ F.Z.; AZEREDO‚ J.B.; BRAGA‚ A.L.; LÜDTKE‚ D.S.; PAIXÃO‚ M.W.. Organocatalytic asymmetric aldol reactions mediated by a cysteine-derived prolinamide. Tetrahedron Letters, v. 49, n. 34, p. 5094-5097, 2008. (07/02382-7)

BRAGA, HUGO C.; WOUTERS, ANA D.; ZERILLO, FELIPE B.; LUEDTKE, DIOGO S.. Synthesis of seleno-carbohydrates derived from D-galactose. Carbohydrate Research, v. 345, n. 16, p. 2328-2333, NOV 2 2010. (07/02382-7)

BRAGA, HUGO C.; STEFANI, HELIO A.; PAIXAO, MARCIO W.; SANTOS, FRANCIELLI W.; LUEDTKE, DIOGO S.. Synthesis of 5 '-seleno-xylofuranosides. Tetrahedron, v. 66, n. 19, p. 6-pg., 2010-05-08. (07/02382-7)