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A synthetic and structural study of some glycosylamines and related compounds

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dc.contributor.author Boolieris, Dennis Steve
dc.date.accessioned 2011-03-16T22:32:49Z
dc.date.accessioned 2022-10-25T05:45:32Z
dc.date.available 2011-03-16T22:32:49Z
dc.date.available 2022-10-25T05:45:32Z
dc.date.copyright 1973
dc.date.issued 1973
dc.identifier.uri https://ir.wgtn.ac.nz/handle/123456789/23330
dc.description.abstract A synthetic route of possible general applicability for the preparation of N-glycosylated β-aminothiols was explored. Treatment of 2-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-benzthiazoline with mercury (II) acetate gives di-(N-D-glucofuranosyl-o-amino-benzenethiol)-mercury (II). Acetylation of this chelate gives the tetra-O-acetate which on removal of the mercury gives di-(N-2,3,5,6-tetra-O-acetyl-D-glucofuranosyl-o-aminophenyl)-disulphide and N-(2,3,5,6-tetra-O-acetyl-D-glucofuranosyl)-o-aminobenzenethiol under oxidizing and non-oxidizing conditions, respectively. The mercaptofuranosylamine was then converted to the S-acetyl and N,S-diacetyl derivatives. The rearrangements of the above benzthiazoline and 2-(D-gluco-1,2,3,4,5-pentahydroxypentyl)-thiazolidine-4-carboxylic acid with nickel (II) acetate were briefly investigated. The possibility of synthesizing 1-N-glycosylated-cystinyl peptides by use of the metal ion induced rearrangement of thiazol-idines is proposed. Attempted synthesis of N-glycosylated β-aminothiols by condensation of S-benzyl-L-cysteine with D-glucose or by rearrangement of o-aminophenyl 1-thio-β-D-glucopyranoside failed to give the desired products. en_NZ
dc.format pdf en_NZ
dc.language en_NZ
dc.language.iso en_NZ
dc.publisher Te Herenga Waka—Victoria University of Wellington en_NZ
dc.title A synthetic and structural study of some glycosylamines and related compounds en_NZ
dc.type Text en_NZ
vuwschema.type.vuw Awarded Research Masters Thesis en_NZ
thesis.degree.discipline Chemistry en_NZ
thesis.degree.grantor Te Herenga Waka—Victoria University of Wellington en_NZ
thesis.degree.level Masters en_NZ

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