Role of hydroxyl group on the mesomorphism of alkyl glycosides:synthesis and thermal behavior of alkyl 6-deoxy-beta-D-glucopyranosides
Data(s) |
01/06/2010
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Resumo |
A homologous series of alkyl 6-deoxy-beta-D-glucopyranoside amphiphiles was prepared,in an effort to identify the role of hydroxyl group in the mesomorphic behavior of alkyl glycosides. Synthesis was performed by a chlorination of the sugar moiety in alkyl-beta-D-glucopyranosides with methylsulfonyl chloride in DMF, followed by a metal mediated dehalogenation to secure alkyl 6-deoxy-beta-D-glucopyranosides, wherein the alkyl chain length varied from C-9 to C-16. The mesomorphic behavior of these 6-deoxy alkyl glycosides was assessed using polarizing optical microscopy, differential scanning calorimetry and X-ray diffraction method. Whereas the lower homologues exhibited a monotropic SmA phase till sub-ambient temperatures, the higher homologues formed a plastic phase. A partial interdigitized bilaye structure of SmA phase is inferred from experimental d-spacing and computationally derived lengths of the molecules. The results were compared with those of normal alkyl glucopyranosides, retained with hydroxyl groups at C-2-C-6 carbons, and alkyl 2-deoxy-glucopyranosides, devoid of a hydroxyl group at C-2 and the comparison showed important differences in the mesomorphic behavior.(C)2010 Elsevier Ireland Ltd. All rights reserved. |
Formato |
application/pdf |
Identificador |
http://eprints.iisc.ernet.in/31221/1/role.pdf Singh, Madan Kumar and Jayaraman, Narayanaswamy and Rao, Shankar DS and Prasad, Krishna S (2010) Role of hydroxyl group on the mesomorphism of alkyl glycosides:synthesis and thermal behavior of alkyl 6-deoxy-beta-D-glucopyranosides. In: Chemistry and Physics of Lipids, 163 (6). pp. 580-585. |
Publicador |
Elsevier Science |
Relação |
http://dx.doi.org/10.1016/j.chemphyslip.2010.04.006 http://eprints.iisc.ernet.in/31221/ |
Palavras-Chave | #Organic Chemistry |
Tipo |
Journal Article PeerReviewed |