139499-19-7

Upstream product

• 124330-54-7 (1S,4R,5S,6S)-4,5,6-tris(benzyloxy)-3-((benzyloxy)methyl)-N-((1S,2S,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-((benzyloxy)methyl)cyclohexyl)cyclohex-2-enamine 
• 37248-47-8 validamycin A 
• 38665-10-0 (+)-validoxylamine A 
• 124330-57-0 (2R,3S,4R,5R)-2,3,4-tris(benzyloxy)-5-[(benzyloxy)methyl]cyclohexanone 

Downstream Products

• 124330-55-8 N-((1S,2S,3S,4R,5R)-2,3,4-Tris-benzyloxy-5-benzyloxymethyl-cyclohexyl)-acetamide 
• 139499-25-5 <(1S)-(1,2,4/3,5)-4-acetoxy-5-acetoxymethyl-2,3-dibenzyloxycyclohexyl><(1S)-(1,2,4/3,5)-2,3,4-tribenzyloxy-5-(benzyloxymethyl)cyclohexyl>amine 
• 139877-35-3 bis<(1S)-(1,2,4/3,5)-2,3,4-tribenzyloxy-5-(benzyloxymethyl)cyclohexyl>amine 

Relevant academic research and scientific papers

Pseudoglycosyltransferase catalyzes nonglycosidic C-N coupling in validamycin a biosynthesis

Glycosyltransferases are ubiquitous in nature. They catalyze a glycosidic bond formation between sugar donors and sugar or nonsugar acceptors to produce oligo/polysaccharides, glycoproteins, glycolipids, glycosylated natural products, and other sugar-containing entities. However, a trehalose 6-phosphate synthase-like protein has been found to catalyze an unprecedented nonglycosidic C-N bond formation in the biosynthesis of the aminocyclitol antibiotic validamycin A. This dedicated 'pseudoglycosyltransferase catalyzes a condensation between GDP-valienol and validamine 7-phosphate to give validoxylamine A 7′-phosphate with net retention of the 'anomeric configuration of the donor cyclitol in the product. The enzyme operates in sequence with a phosphatase, which dephosphorylates validoxylamine A 7′-phosphate to validoxylamine A.

Synthesis of trehazolin analogues containing modified sugar moieties

In order to elucidate the biological roles of the sugar moiety of the trehalase inhibitor trehazolin 1, the sugar portion was first replaced with hydrophobic aromatic functions, providing the N-phenyl 3 and N-benzyl derivatives 4 of trehazolin 1.Then the six analogues with the sugar moiety being replaced with D-mannopyranose 5, 3-deoxy-ribo-hexopyranose 6, D-galactopyranose 7, 6-deoxy-D-glucopyranose 8, 5a-carba-α-D-glucopyranose 9 and 5a-carba-α-D-xylo-hex-5(5a)-enopyranose residues 10 were synthesized.In the hope of improving the fungicidal activity of trehazolin 1. we prepared two disaccharide analogues, 11 and 12, containing maltose and cellobiose residues.A remarkable decrease in potency was observed in the analogues 5-8 and 10, but not for 5a'-carbatrehazolin 9, suggesting an essential role for the D-gluco configuration of the hexopyranose portion.The β-D-glucosyl analogue 12 showed an increase in antifungal activity against Rhizoctonia solani, as compared with that of trehazolin 1.The nalogues 3 and 4 were not trehalase inhibitors, but rather were moderate α-glucosidase inhibitors.

Cleavage of Validoxylamine A Derivatives with N-Bromosuccinimide: Preparation of Blocked Synthons Useful for the Construction of Carba-oligosaccharides Composed of Imino-Linkages

Reaction of validoxylamine A and several of its derivatives with N-bromosuccinimide proceeded through cleavage of the imino bonds to give rise to the synthetically useful blocked derivatives of valienamine and validamine, and the cyclohexanone and cyclohe