The synthesis and conformational analysis of pseudo-thio-1,2-dimannoside are described. This molecule mimics mannobioside (Manα(1,2)Man) and is an analog of pseudo-1,2-dimannoside, with expected increased stability to enzymatic hydrolysis. A short and efficient synthesis was developed based on an epoxide ring-opening reaction by a mannosyl thiolate, generated in situ from the corresponding thioacetate. NMR-NOESY studies supported by MM3∗ calculations showed that the pseudo-thio-1,2-dimannoside shares the conformational behavior of the pseudo-1,2-dimannoside and is a structural mimic of the natural disaccharide. Its affinity for DC-SIGN was measured by SPR and found to be comparable to the corresponding O-linked analog, offering good opportunities for further developments.

Facile access to pseudo-thio-1,2-dimannoside, a new glycomimetic DC-SIGN antagonist / A. Tamburrini, S. Achilli, F. Vasile, S. Sattin, C. Vivès, C. Colombo, F. Fieschi, A. Bernardi. - In: BIOORGANIC & MEDICINAL CHEMISTRY. - ISSN 1464-3391. - 25:19(2017 Oct 01), pp. 5142-5147. [10.1016/j.bmc.2017.03.046]

Facile access to pseudo-thio-1,2-dimannoside, a new glycomimetic DC-SIGN antagonist

A. Tamburrini;F. Vasile;S. Sattin;C. Colombo;A. Bernardi
2017-10-01

Abstract

The synthesis and conformational analysis of pseudo-thio-1,2-dimannoside are described. This molecule mimics mannobioside (Manα(1,2)Man) and is an analog of pseudo-1,2-dimannoside, with expected increased stability to enzymatic hydrolysis. A short and efficient synthesis was developed based on an epoxide ring-opening reaction by a mannosyl thiolate, generated in situ from the corresponding thioacetate. NMR-NOESY studies supported by MM3∗ calculations showed that the pseudo-thio-1,2-dimannoside shares the conformational behavior of the pseudo-1,2-dimannoside and is a structural mimic of the natural disaccharide. Its affinity for DC-SIGN was measured by SPR and found to be comparable to the corresponding O-linked analog, offering good opportunities for further developments.
DC-SIGN; Glycomimetics; Mannobioside; NOESY; Thioglycosides
Settore CHIM/06 - Chimica Organica
Development of Selective Carbohydrate Immunomodulators Targeting C-type Lectin Receptors on Antigen Presenting Cells
22-mar-2017
Article (author)
File in questo prodotto:
File Dimensione Formato  
1-s2.0-S0968089617305783-main.pdf

accesso aperto

Tipologia: Publisher's version/PDF
Dimensione 1.1 MB
Formato Adobe PDF
1.1 MB Adobe PDF Visualizza/Apri
Pubblicazioni consigliate

Caricamento pubblicazioni consigliate

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/527385
Citazioni
  • ???jsp.display-item.citation.pmc??? 3
  • Scopus 9
  • ???jsp.display-item.citation.isi??? 8
social impact