1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside - CAS 10022-13-6
Category:
Carbohydrates
Product Name:
1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside
Synonyms:
2-Deoxy-2-N-phthalimido-1,3,4,6-tetra-O-acetyl-b-D-glucopyranose
CAS Number:
10022-13-6
Molecular Weight:
477.42
Molecular Formula:
C22H23NO11
COA:
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MSDS:
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Structure:
Monosaccharides
Chemical Structure
CAS 10022-13-6 1,3,4,6-Tetra-O-acetyl-2-deoxy-2-phthalimido-b-D-glucopyranoside

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Reference Reading


1.Synthesis of 2-amino-2-deoxy-beta-glycosyl-(1-->5)-nucleosides and the interaction with RNA.
Zhang G1, Guan Z, Zhang L, Min J, Zhang L. Bioorg Med Chem. 2003 Jul 31;11(15):3273-8.
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranose and 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-beta-D-galactopyranose reacted with protected nucleosides in the presence of BF(3) as promoter at room temperature to give selectively 2-amino-2-deoxy-beta-glycosyl (1-->5)nucleosides in good yields. CD spectra and thermal melting studies showed that 2-amino-2-deoxy-beta-D-glucopyranosyl-(1-->5)-nucleosides could interact with RNA in solution and 2-deoxy-2-amino-beta-D-galactopyranosyl-(1-->5)-nucleosides (17-19) exhibit higher affinity to RNA than 2-deoxy-2-amino-beta-D-glucopyranosyl-(1-->5)-nucleosides (14-16). It indicated that the majority of interactions are established between the polar group of glycosylnucleosides and the sugar-phosphate backbone of RNA helices and weak stacking interaction is observed. The different configuration of hydroxyl group on the glycosyl moiety may affect the glycosyl-nucleoside binding to RNA by induced fit.