129492-77-9

Upstream product

• 100896-15-9 methyl 2-azido-2-deoxy-α-D-lyxofuranoside 
• 105878-97-5 (2R,3R,4R)-N-benzyloxycarbonyl-2-(hydroxymethyl)pyrrolidine-3,4-diol 
• 67561-03-9 N-benzyloxycarbonylglycinal 
• 7045-40-1 Methyl 3,5-O-Isopropylidene-α-D-xylofuranoside 
• 110088-79-4 methyl 2-azido-2-deoxy-5-O-p-toluenesulphonyl-α-D-lyxofuranoside 
• 110088-78-3 methyl 3,5-O-isopropylidene-2-O-trifluoromethanesulphonyl-α-D-xylofuranoside 
• 100806-50-6 methyl 2-azido-2-deoxy-3,5-O-isopropylidene-α-D-lyxofuranoside 
• 129961-19-9 (1R,3S,4S,7R)-3-Methoxy-2-oxa-5-aza-bicyclo[2.2.1]heptan-7-ol 
• 100806-51-7 methyl N-benzyloxycarbonyl-2,5-dideoxy-2,5-imino-α-D-lyxofuranoside 

Downstream Products

• 1427173-62-3 (2R,3R,4R)-N-benzyloxycarbonyl-2-((benzylamino)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-67-8 (2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-(1-methyl-1H-benzo[d]imidazol-2-yl)pyrrolidine 
• 1427173-70-3 (2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-(((2-hydroxyethyl)amino)methyl)pyrrolidine 
• 1427174-26-2 (2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-(((3-hydroxypropyl)amino)methyl)pyrrolidine 
• 1427173-73-6 (2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-((((S)-1-hydroxypropan-2-yl)amino)methyl)pyrrolidine 
• 1427174-27-3 (2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-((((S)-1-hydroxybutan-2-yl)amino)methyl)pyrrolidine 
• 1427174-29-5 (2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-((((R)-1-hydroxypentan-2-yl)amino)methyl)pyrrolidine 
• 1427173-77-0 (2R,3R,4R)-N-benzyloxycarbonyl-3,4-dihydroxy-2-((((R)-1-hydroxy-3-methylbutan-2-yl)-amino)methyl)pyrrolidine 
• 1427173-79-2 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((1,3-dihydroxypropan-2-yl)amino)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-81-6 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((2R,3R,4R)-3,4-dihydroxy-2-(hydroxymethyl)piperidin-1-yl)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-83-8 (2R,3R,4R)-N-benzyloxycarbonyl-2-((glycineamidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-85-0 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((S)-alanineamidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427174-30-8 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((S)-leucineamidyl)methyl)-3,4-dihydroxypyrrolidine 
• 1427173-87-2 (2R,3R,4R)-N-benzyloxycarbonyl-2-(((S)-phenylalanineamidyl)methyl)-3,4-dihydroxypyrrolidine 

Relevant academic research and scientific papers

Casuarine stereoisomers from achiral substrates: Chemoenzymatic synthesis and inhibitory properties

A straightforward chemoenzymatic synthesis of four uncovered casuarine stereoisomers is described. The strategy consists of l-fuculose-1-phosphate aldolase F131A-variant-catalyzed aldol addition of dihydroxyacetone phosphate to aldehyde derivatives of 1,4-dideoxy-1,4-imino-d-arabinitol (DAB) and its enantiomer (LAB) and subsequent one-pot catalytic deprotection-reductive amination. DAB and LAB were obtained from dihydroxyacetone and aminoethanol using d-fructose-6-phosphate aldolase and l-rhamnulose-1-phosphate aldolase catalysts, respectively. The new ent-3-epi-casuarine is a strong inhibitor of α-d-glucosidase from rice and of rat intestinal sucrase.

Chemo-enzymatic synthesis and glycosidase inhibitory properties of DAB and LAB derivatives

A chemo-enzymatic strategy for the preparation of 2-aminomethyl derivatives of (2R,3R,4R)-2-(hydroxymethyl)pyrrolidine-3,4-diol (also called 1,4-dideoxy-1,4-imino-d-arabinitol, DAB) and its enantiomer LAB is presented. The synthesis is based on the enzymatic preparation of DAB and LAB followed by the chemical modification of their hydroxymethyl functionality to afford diverse 2-aminomethyl derivatives. This strategy leads to novel aromatic, aminoalcohol and 2-oxopiperazine DAB and LAB derivatives. The compounds were preliminarily explored as inhibitors of a panel of commercial glycosidases, rat intestinal disaccharidases and against Mycobacterium tuberculosis, the causative agent of tuberculosis. It was found that the inhibitory profile of the new products differed considerably from the parent DAB and LAB. Furthermore, some of them were active inhibiting the growth of M. tuberculosis.

POTENT COMPETITIVE INHIBITION OF &α-GALACTOSIDASE AND &α-GLUCOSIDASE ACTIVITY BY 1,4-DIDEOXY-1,4-IMINOPENTITOLS: SYNTHESES OF 1,4-DIDEOXY-1,4-IMINO-D-LYXITOL AND OF BOTH ENANTIOMERS OF 1,4-DIDEOXY-1,4-IMINOARABINITOL

The syntheses of 1,4-dideoxy-1,4-imino-D-lyxitol (3), 1,4-dideoxy-1,4-imino-D-arabinitol (4) and 1,4-dideoxy-1,4-imino-L-arabinitol (5) are reported; (3) is a potent competitive inhibitor of α-galactosidase (green coffee beans) and (4) a competitive inhibitor of α-glucosidase (Brewer's yeast) suggesting that iminopentitols have considerable potential as glycosidase inhibitors. (4) was found to be identical to an alkaloid recently isolated from Angylocalyx boutiqueanus.