133697-32-2

Upstream product

• 153373-83-2 N-((1R,2R,3S)-1-Formyl-2,3,5-trihydroxy-4-oxo-pentyl)-acetamide 
• 130609-21-1 2-acetamido-1,2,5-trideoxy-1,5-imino-D-glucitol hydrochloride 
• 1401914-68-8 2-acetamido-3,6-di-O-acetyl-1-N,4-O-dibenzyl-1,2,5-trideoxy-1,5-imino-D-glucitol 
• 1401914-66-6 3,6-di-O-acetyl-2-azido-1-N,4-O-dibenzyl-1,2,5-trideoxy-1,5-imino-D-glucitol 
• 114129-23-6 N-benzyl-1,5-dideoxy-1,5-imino-4,6-O-isopropylidene-D-mannitol 
• 19130-96-2 1,5-dideoxy-1,5-imino-D-glucitol 
• 180626-63-5 2-azido-3,4,6-tri-O-benzyl-N-benzyloxycarbonyl-1,2,5-trideoxy-1,5-imino-D-glucitol 
• 180626-64-6 (2R,3R,4R,5S)-5-Acetylamino-3,4-bis-benzyloxy-2-benzyloxymethyl-piperidine-1-carboxylic acid benzyl ester 
• 919474-81-0 N-((3S,4R,5R,6R)-1-benzhydryl-4,5-dihydroxy-6-(hydroxymethyl)piperidin-3-yl)acetamide 
• 105266-03-3 N-((3S,4R,5R,6R)-5-Benzyloxy-4-hydroxy-6-hydroxymethyl-piperidin-3-yl)-acetamide 
• 114040-94-7 2-acetamido-1,2,5-trideoxy-1,5-imino-4,6-O-isopropylidene-D-glucitol 
• 105266-02-2 2-acetamido-N-benzyloxycarbonyl-4-O-benzyl-1,5-imino-1,2,5-trideoxy-D-glucitol 
• 1132966-60-9 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactitol 

Downstream Products

• 121701-87-9 2-acetamido-1-N-benzyl-1,2,5-trideoxy-1,5-imino-D-galactitol 
• 114040-97-0 N-((3S,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-1-methylpiperidin-3-yl)acetamide 
• 1401914-31-5 1N-methyl-2-acetamido-1,2,5-trideoxy-1,5-imino-D-galactitol 

Relevant academic research and scientific papers

Stereoselective synthesis of 2-acetamido-1,2-dideoxynojirimycin (DNJNAc) and ureido-DNJNAc derivatives as new hexosaminidase inhibitors

2-Acetamido-1,2-dideoxyiminosugars are selective and potent inhibitors of hexosaminidases and therefore show high therapeutic potential for the treatment of various diseases, including several lysosomal storage disorders. A stereoselective synthesis of 2-

OLIGONUCLEOTIDE COMPOSITIONS AND METHODS THEREOF

The present disclosure provides modified oligonucleotides and compositions and methods thereof. In some embodiments, provided technologies comprise modified sugars and/or modified internucleotidic linkages. In some embodiments, the present disclosure provides technologies for preparing modified oligonucleotides. In some embodiments, the present disclosure provides chirally controlled oligonucleotide compositions and methods for their preparation and uses.

Integrating thin film microfluidics in developing a concise synthesis of DGJNAc: A potent inhibitor of α-N-acetylgalctosaminidases

A simple synthesis, which utilizes a thin film microfluidic reactor for a problematic step, of a potent inhibitor of α-N-acetylhexosaminidases, DGJNAc, has been developed.

Compounds And Methods For The Treatment Of Alzheimer's Disease And/Or Cerebral Amyloid Angiopathy

Described herein are novel compounds and methods for the treatment and/or prevention of cerebral amyloidoses such as Alzheimer's disease (AD) and/or cerebral amyloid angiopathy (CAA).

Stereoselective synthesis of 2-acetamido-1,2-dideoxyallonojirimycin (DAJNAc), a new potent hexosaminidase inhibitor

A practical synthesis of the previously unreported N-acetyl-d-allosamine glycomimetic DAJNAc is described. The reaction sequence involves Pd-catalyzed allylic substitution by phthalimide in an azaheterobicyclic scaffold as the key step. The new iminosugar resulted in being a stronger β-N- acetylglucosaminidase (human placenta) competitive inhibitor than the d-gluco (DNJNAc) and d-galacto (DGJNAc) stereoisomers.

The development of selective inhibitors of nagz: Increased susceptibility of gram-negative bacteria to β-lactams

The increasing incidence of inducible chromosomal AmpC β-lactamases within the clinic is a growing concern because these enzymes deactivate a broad range of even the most recently developed β-lactam antibiotics. As a result, new strategies are needed to block the action of this antibiotic resistance enzyme. Presented here is a strategy to combat the action of inducible AmpC by inhibiting the β-glucosaminidase NagZ, which is an enzyme involved in regulating the induction of AmpC expression. A divergent route facilitating the rapid synthesis of a series of N-acyl analogues of 2-acetamido-2-deoxynojirimycin is reported here. Among these compounds are potent NagZ inhibitors that are selective against functionally related human enzymes. These compounds reduce minimum inhibitory concentration values for β-lactams against a clinically relevant Gram-negative bacterium bearing inducible chromosomal AmpC β-lactamase, Pseudomonas aeruginosa. The structure of a NagZ-inhibitor complex provides insight into the molecular basis for inhibition by these compounds. The development of selective and potent inhibitors of the β-glucosaminidase NagZ, which is an important enzyme in AmpC β-lactamase expression, based on the inhibitor 2-acetamido-2-deoxynojirimycin is described. In addition, the structure of a NagZ-inhibitor complex provides insight into the molecular basis for inhibition by these compounds.

Scalable syntheses of both enantiomers of DNJNAc and DGJNAc from glucuronolactone: The effect of N-alkylation on hexosaminidase inhibition

The efficient scalable syntheses of 2-acetamido-1,2-dideoxy-D-galacto- nojirimycin (DGJNAc) and 2-acetamido-1,2-dideoxy-D-gluco-nojirimycin (DNJNAc) from D-glucuronolactone, as well as of their enantiomers from L-glucuronolactone, are reported. The evaluation of both enantiomers of DNJNAc and DGJNAc, along with their N-alkyl derivatives, as glycosidase inhibitors showed that DGJNAc and its N-alkyl derivatives were all inhibitors of α-GalNAcase but that none of the epimeric DNJNAc derivatives inhibited this enzyme. In contrast, both DGJNAc and DNJNAc, as well as their alkyl derivatives, were potent inhibitors of β-GlcNAcases and β-GalNAcases. Neither of the L-enantiomers showed any significant inhibition of any of the enzymes tested. Correlation of the in vitro inhibition with the cellular data, by using a free oligosaccharide analysis of the lysosomal enzyme inhibition, revealed the following structure-property relationship: hydrophobic side-chains preferentially promoted the intracellular access of iminosugars to those inhibitors with more-hydrophilic side-chain characteristics. Getting the NAc of it: Scalable syntheses of DGJNAc and DNJNAc from D-glucuronolactone are reported. DGJNAc and its N-alkyl derivatives were inhibitors of α-GalNAcase and both DGJNAc and DNJNAc were potent inhibitors of β-GlcNAcases and β-GalNAcases. Copyright

SYNTHESIS OF DGJNAC FROM D-GLUCURONOLACTONE AND USE TO INHIBIT ALPHA-N-ACETYLGALACTOSAMINIDASES

A convenient and scalable synthesis of DGJNAc ID from D-glucuronolactone in an overall yield of 20% is provided. DGJNAc is the first highly potent and specific competitive inhibitor of GalNAcases. DGJNAc ID is also a competitive inhibitor of -hexosaminida

Synthesis of 2-acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc] from d-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases

2-Acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc], prepared in 20% overall yield from d-glucuronolactone, is the first potent competitive sub-micromolar inhibitor of α-N-acetyl-galactosaminidases (Ki 0.081 μM from chicken liver, Ki 0.136 μM from Charonia lampas). DGJNAc is a good competitive-whereas the enantiomer l-DGJNAc is a very weak but non-competitive-inhibitor of β-hexosaminidases.

1,5-Dideoxy-1,5-imino-D-glucitol Compounds

1,5-Dideoxy-1,5-imino-D-glucitol compounds as shown in the specification. Also disclosed is a method of treating a hexosaminidase-associated disease.