2. Results and discussion 1. Introduction Abstract INDEX

Index

1

INDEX

Abstract

1. Introduction

1.1 DENTRITIC CELLS pag. 4 1.2 DC-SIGN, A DC-SPECIFIC C-TYPE LECTIN pag. 5 1.3 DC-SIGN STRUCTURE pag. 7 1.4 DC-SIGN AS AG RECEPTOR ON DCS pag. 9 1.5 DC-SIGN AS A NOVEL HIV-RECEPTOR pag. 10 1.6 THE STRUCTURAL BASIS OF DC-SIGN’S CRD

DOMAIN. pag.12

1.7 BINDING OF MONOVALENT DC-SIGN ANTAGONIST pag. 14

1.7.1 The choice of monosaccharide unit pag. 15 1.7.2 The choice of glycosydic bond surrogate pag. 18 1.7.3 The choice of adjacent structure that contribute to overall binding affinity pag.18

1.8 PSEUDO-1,2-MANNOBIOSIDES:AN ADEQUATE

STRATEGY ON DC-SIGN ANTAGONISM pag. 22 1.8.1 Synthesis of pseudo-1,2-mannobiosides pag. 24 1.8.2 NMR, Docking and infection studies pag. 29

2. Results and discussion

Index

2 2.2 PURPOSES OF THE THESIS pag. 36

2.3 SYNTHESIS OF THE KEY INTERMEDIATE: 6-O-BENZYL-

5A-CARBA-β-D-MANNOPYRANOSE (+)-2.13 pag. 38

2.3.1 Stereoselective synthesis of the carba alcohol (+)-2.10 pag. 38 2.3.2 Obtainment of the key intermediate (+)-2.13 pag. 44

2.4 SYNTHESIS OF THE 2-AMINOETHYL-

PSEUDOMANNOBIOSIDE (+)-2.14 pag. 48

2.5 SYNTHESIS OF THE 2-AZIDOETHYL-

PSEUDOMANNOBIOSIDE (-)-2.15a pag. 59

2.6 INFECTION STUDIES pag. 64

3.

Experimental

3.1 1H NMR SPECTRA pag. 84

4. References