4704-17-0

Upstream product

• 31281-57-9 3,4,6-tri-O-acetyl-2--2-deoxy-1-O-methyl-β-D-glucopyranoside 
• 42854-52-4 methyl O-3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 67-56-1 methanol 
• 3006-58-4 2-carbobenzyloxyamino-2-deoxy-D-glucopyranose 
• 4710-88-7 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide hydrobromide 
• 16684-31-4 2-benzyloxycarbonylamino-2-deoxy-D-glucose 

Relevant academic research and scientific papers

Regioselective sulfamoylation at low temperature enables concise syntheses of putative small molecule inhibitors of sulfatases

Regioselective sulfamoylation of primary hydroxyl groups enabled a 5-step synthesis (overall yield 17%) of the first reported small molecule inhibitor of sulfatase-1 and 2, ((2S,3R,4R,5S,6R)-4,5-dihydroxy-2-methoxy-6-((sulfamoyloxy)methyl)tetrahydro-2H-pyran-3-yl)sulfamic acid, which obviated the use of hydroxyl protecting groups and is a marked improvement on the reported 9-step synthesis (overall yield 9%) employing hazardous trifluoromethylsulfonyl azide. The sulfamoylation methodology was used to prepare a range of derivatives of 1, and inhibition data was generated for Sulf-2, ARSA and ARSB.

Hybrid aminoglycoside antibiotics via tsuji palladium-catalyzed allylic deoxygenation

Biosynthetically inspired manipulation of the antibiotic paromomycin led, in six high-yielding steps, to a ring A harboring an R,β-unsaturated 6′- aldehyde and an allylic 3′-methylcarbonate group. Tsuji deoxygenation in the presence of 5 mol % Pd2(dba)3 and Bu3P granted access to a novel series of 3′,4′-dideoxy- 4′,5′-dehydro ring A hybrids. The neomycin-sisomicin hybrid exhibited superior in vitro antibacterial activity to the parent compound neomycin.

Synthesis and conformational analysis of linear and cyclic peptides containing sugar amino acids

Sugar amino acids (SAAs) were designed and synthesized as new non-peptide peptidomimetics utilizing carbohydrates as peptide building blocks. They represent sugar-like ring structures that carry an amino and a carboxylic functional group and have a specific conformational influence on the backbone of peptides due to their distinct substitution patterns in rigid pyranose sugar rings. Five different SAAs (SAA1α, SAA1β, SAA2, SAA3, and SAA4) have been synthesized that show the ability to constrain linear backbone conformations or distinct turn structures. Linear and cyclic peptides involving SAAs have been prepared in solution as well as by solid phase synthesis. SAA1α and SAA2 were incorporated into two linear Leu-enkephalin analogs, replacing the natural Gly-Gly dipeptide. NMR studies provide evidence for the conformation-inducing effect of the carbohydrate moiety. SAA2 and SAA3 have been placed in cyclic hexapeptide analogs of somatostatin; SAA4 was incorporated in a model peptide. The conformation of the cyclic peptides cyclo(-SAA2-Phe-D-Trp-Lys-Thr-), cyclo(-SAA3-Phe-D-Trp-Lys(Boc)-Thr(tBu)-), and cyclo(-SAA4-Ala-D-Pro-Ala-Ala-) have been analyzed by various NMR techinques in combination with distance geometry calculations and subsequent molecular dynamic simulations. The determined solution conformations were compared to representative idealized peptide backbones. SAA2 and SAA3 induce a β-turn structure while SAA4 mimics a γ-turn. Both enkephalin analogs were not active in the guinea pig ileum assay. The somatostatin analog containing SAA2 has an inhibition constant (IC50) of 0.15 μM for the inhibition of the release of growth hormone.