Alpha-(1-->2)-, and alpha-(1-->3)-, and alpha-(1-->6)-linked thioglycosidic disaccharides: syntheses and anti-HIV testing of thiokojibiose octaacetate, thionigerose, and thioisomaltose.
The syntheses of several alpha-linked thioglycosidic disaccharides are described, including thiokojibiose octaacetate (1), thionigerose (2), and thioisomaltose (3). The title compounds were synthesized by coupling 2,3,4,6-tetra-O-acetyl-1.5-acetyl-1-thio-alpha-D-glucopyranose (4) with either 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethylsulfonyl-beta-D-manno pyr anose (7), 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethylsulfonyl-alpha-D-++ +allofuranose (15), or methyl 2,3,4-tri-O-acetyl-6-deoxy-6-iodo-alpha-D-glucopyranoside (17), respectively. Thiokojibiose octaacetate in turn was converted to 3,4,6-tri-O-acetyl-2-S-(2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl)-2 -thio-alpha-D-glucopyranosyl bromide (9), which was used to obtain several related disaccharides and one trisaccharide. All of the compounds, including thiomaltose and thiotrehalose, which were resynthesized by known methods, were tested for their anti-HIV activity in either CEM or MT-2 cells. Anti-HIV activity was noted only with thiokojibiose octaacetate and its 1-thio analogue (14), which had IC50 values of 51 and 48 micrograms/mL in CEM cells, respectively.
Comber
R N
RN
Organic Chemistry Department, Southern Research Institute, Birmingham, Alabama 35255-5305.
Friedrich
J D
JD
Dunshee
D A
DA
Petty
S L
SL
Secrist
J A
JA
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002460:Cell Line; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006678:HIV / Q000187:drug effects*; D007534:Isomaltose / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000494:pharmacology; D008969:Molecular Sequence Data; D013863:Thioglucosides / Q000138:chemical synthesis / Q000494:pharmacology
D000998:Antiviral Agents; D004187:Disaccharides; D013863:Thioglucosides; C090603:methyl thioisomaltose; C090605:thiokojibiose octaacetate; C090604:thionigerose; D007534:Isomaltose