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dc.contributor.authorMilah, Khatma
dc.date.accessioned2018-11-14T19:15:21Z
dc.date.available2018-11-14T19:15:21Z
dc.identifier.urihttp://hdl.handle.net/10464/13767
dc.description.abstractThe present study describes the synthesis of 3’,5’- cyclic diguanylic acid (c-di-GMP), attempts were made to synthesize guanosine bearing a 2’-O-(hexyn-6-yl)- and 2’-O-(6-azidohexyl)-modification using 2,6-diaminopurine riboside as starting material. The synthesis of 2’-O-(hexyn-6-yl) guanosine started with the alkylation of 2,6-diaminopurine riboside with 6-iodo-1-hexyne, which gave a mixture of 2’- and 3’-O-alkylated 2,6-diaminopurine riboside. Treatment of this product with isobutyryl chloride, followed by ammonium hydroxide gave N2-isobutyryl-2’-O-2’-O-(hexyn-6-yl)-2,6-diaminopurine riboside. Subsequent deamination reaction was carried out with sodium nitrite in a mixed solvent gave the desired N2-isobutyryl-2’-O-2’-O-(hexyn-6-yl) guanosine. N2-Isobutyryl-2’-O-(6-azidohexyl) guanosine was also obtained in the similar manner. Synthesis of a second building block, a suitably protected guanosine H-phosphonate was also attempted using guanosine as starting material. Experimental and spectral data are provided for new compounds.en_US
dc.language.isoengen_US
dc.publisherBrock Universityen_US
dc.subjectc-di-GMP, vaccine adjuvant ,STING protein,en_US
dc.titleSynthesis of 3’, 5’-cyclic diguanylic acid (c-di-GMP) as mucosal vaccine adjuvant and bacterial second messengeren_US
dc.typeElectronic Thesis or Dissertationen_US
dc.degree.nameM.Sc. Chemistryen_US
dc.degree.levelMastersen_US
dc.contributor.departmentDepartment of Chemistryen_US
dc.degree.disciplineFaculty of Mathematics and Scienceen_US
refterms.dateFOA2018-10-20T00:00:00Z


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