7284-37-9

Usage

Uses

beta-D-Glucopyranosylamine

InChI:InChI=1/C6H13NO5/c7-6-5(11)4(10)3(9)2(1-8)12-6/h2-6,8-11H,1,7H2/t2-,3-,4+,5-,6?/m1/s1

Upstream product

• 492-61-5 β-D-glucose 
• 20379-59-3 D-glucopyranosyl azide 
• 2280-44-6 D-Glucose 
• 50-99-7 D-glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 13992-25-1 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 
• 525589-11-1 2-methyl-4,5-dihydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline 
• 849367-23-3 (3aS,5R,6S,7S,7aR)-5-Hydroxymethyl-2-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[2,3-d]oxazole-6,7-diol 
• 100639-11-0 N-(β-D-glucopyranosyl)triphenylphosphine imide 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 

Downstream Products

• 6983-36-4 N-acetyl-β-D-glucopyranosylamine 
• 33758-19-9 N-bromoacetyl-β-D-glucopyranosylamine 
• 136860-06-5 N--L-phenylalanyl-L-leucyl>-β-D-glucopyranosylamine 
• 136863-94-0 N-(β-D-glucopyranosyl)-N'-(trans-2-iodocyclohexyl)urea 
• 134403-88-6 N-benzyloxycarbonyl-β-D-glucosylamine 
• 73847-68-4 β-D-glucopyranosyl-p-nitrophenyltriazene 
• 18918-51-9 N-(1-β-D-Glucopyranosyl)-4-nitro-benzamid 
• 15355-08-5 N-benzoyl-2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosylamine 
• 50802-49-8 β-D-glucopyranosyl isothiocyanate 
• 5513-36-0 2-amino>-2-deoxy-D-glucopyranose 
• 368886-89-9 (1,2-dideoxy-β-D-glucopyranoso)[1,2-d]-1,3-oxazolidine-2-thione 
• 76799-04-7 1-Benzyl-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl)-thiourea 
• 58484-07-4 1-(2-chloroethyl)-3-(β-D-glucopyranosyl)-1-nitrosourea 
• 368886-93-5 N,N'-bis(β-D-glucopyranosyl)thiourea 

Relevant academic research and scientific papers

The effect of monosaccharides on self-assembly of benzenetricarboxamides

The interaction between monosaccharides exhibits an important role in the assembly of monosaccharide-containing molecules. In this work, three common monosaccharides, glucose, galactose and mannose, are employed to investigate the effect of monosaccharide on the self-assembly of benzenetricarboxamide (BTA) core-containing molecules. In the presence of monosaccharides, three benzenetricarboxamide derivatives aggregate into different ordered structures. When alanine linkers are introduced to these molecules between the core and the monosacchride, morphologies of three types of monosaccharide BTAs turned to disordered, meanwhile their structures become similar with the increase of the length of alanine linkers, indicating the disappearance of the monosaccharide effects.

Squaryl group modified phosphoglycolipid analogs as potential modulators of GPR55

Lysophosphatidyl glucoside (LPGlc) is a structurally unique glycolipid that acts as a guidance cue for extending axons during central nervous system development by activating the class A G protein coupled receptor (GPR) 55 of spinal cord sensory axons. GPR55 not only plays an important role during development, but is also implicated in many disease states, rendering molecules that target GPR55 of widespread interest. In this study, we developed synthetic access to a novel class of LPGlc analogues featuring a squaryl diamide group as surrogate for the phosphodiester. We report the facile synthesis of a series of LPGlc analogues, their GPR dependent biological activity and a systematic analysis of the structure-activity relationship in regards to GPR55 modulation. The lead compound featuring identical configuration at all stereocenters compared to natural LPGlc exhibits an activity to repel axons of dorsal root ganglion (DGR) nociceptive neurons.

Small molecule glycoconjugates with anticancer activity

Glycoconjugates are combinations of sugar moieties with organic compounds. Due to their biological resemblance, such structures often have properties that are desirable for drugs. In this study we designed and synthesised several glycoconjugates from smal

Synthesis of β-D-glucopyranuronosylamine in aqueous solution: Kinetic study and synthetic potential

A systematic study of the synthesis of β-D-glucopyranuronosylamine in water is reported. When sodium d-glucuronate was reacted with ammonia and/or volatile ammonium salts in water a mixture of β-D-glucopyranuronosylamine and ammonium N-β-D-glucopyranuronosyl carbamate was obtained at a rate that strongly depended on the experimental conditions. In general higher ammonia and/or ammonium salt concentrations led to a faster conversion of the starting sugar into intermediate species and of the latter into the final products. Yet, some interesting trends and exceptions were observed. The use of saturated ammonium carbamate led to the fastest rates and the highest final yields of β-D-glucopyranuronosylamine/carbamate. With the exception of 1 M ammonia and 0.6 M ammonium salt, after 24 h of reaction all tested protocols led to higher yields of β-glycosylamine/carbamate than concentrated commercial ammonia alone. The mole fraction of α-D-glucopyranuronosylamine/carbamate at equilibrium was found to be 7-8% in water at 30 °C. Concerning bis(β-D-glucopyranuronosyl)amine, less than 3% of it is formed in all cases, with a minimum value of 0.5% in the case of saturated ammonium carbamate. Surprisingly, the reaction was consistently faster in the case of sodium d-glucuronate than in the case of D-glucose (4-8 times faster). Finally, the synthetic usefulness of our approach was demonstrated by the synthesis of three N-acyl-β-D-glucopyranuronosylamines and one N-alkylcarbamoyl-β-D- glucopyranuronosylamine directly in aqueous-organic solution without resorting to protective group chemistry.

Preparation and evaluation of a molecular recognition bionic solid phase extraction column for separation of glucosides

Amolecular recognition bionic solid phase extraction (SPE) column for separation of glucosides has been prepared using a positively charged β-glucosylamidine as the ligand inwhich a glyconmoiety is connected via an N-glycoside linkage. β-Glucosylamidine, highly potent and selective inhibitors of β-glycosidase, is immobilized through a one-step synthesize procedure involving the addition of β-glucosylamine and 2-iminothiolane. HCl simultaneously to a matrix modified with maleimido groups via an appropriate spacer to give a molecular recognition absorbent for β-glucosides. N-octyl-β-D-glucopyranoside and β-D-galactopyranoside or α-D-mannopyranoside was directly chromatographed through the bionic chromatographic column, resulting in a much stronger retention of β-D-glucopyranoside than β-D-galactopyranoside and α-D-mannopyranoside. The retained glucopyranoside could only be eluted by glucose solution. This indicates that the binding of the glucoside was of specific nature that corresponds to the glycon substrate specificity of the glucoside. The ease of preparation and the selective nature of the molecular recognition bionic chromatography should promise a large-scale preparation of the molecular recognition adsorbent for the purification and removal of glucosides according to their glycon substrate specificity.

HOLLOW FIBROUS ORGANIC NANOTUBE AND PRODUCTION METHOD THEREOF

Disclosed is a method of synthesizing a water-free nanotube capable of efficiently encapsulating a functional substance therein, in large quantities. The method comprises: dissolving, in an organic solvent heated up to a temperature equal to or less than a boiling point thereof, an N-glycoside type glycolipid represented by the following general formula (1): G-NHCO—R1 (wherein G represents a sugar residue from which a hemiacetal hydroxyl group bonded to an anomeric carbon atom of the sugar is excluded; and R1 represents an unsaturated hydrocarbon group having 10 to 39 carbon atoms), or a peptide-lipid conjugate represented by one of the following general formulas (2) and (3): R2CO(NH—CHR3—CO)mOH and H(NH—CHR3—CO)mNHR2 (wherein: R2 represents a hydrocarbon group having 6 to 24 carbon atoms; R3 represents an amino-acid side chain; and m represents an integer of 1 to 10); (i) slowly cooling the obtained solution, and maintaining the cooled solution undisturbed at room temperature, or (ii) concentrating the obtained solution, and maintaining the concentrated solution disturbed at room temperature, or (iii) adding to the obtained solution a poor solvent for the N-glycoside type glycolipid or the peptide-lipid conjugate, and maintaining the mixed solution undisturbed at room temperature; collecting from the resulting solution a hollow fibrous organic nanotube formed through self-assembling in the stationary solution, and drying the collected hollow fibrous organic nanotube, in air at room temperature or by heating under reduced-pressure, to obtain a hollow fibrous organic nanotube.

Synthesis and antibacterial activity of aminodeoxyglucose derivatives against Listeria innocua and Salmonella typhimurium

In this study aminodeoxyglucose derivatives were synthesized and evaluated for their antibacterial activity against two food bacteria, Listeria innocua and Salmonella typhimurium. 6-Amino-6-deoxy-α-Dmethylglucopyranose (GSA-6), 3-amino-3-deoxy-D-glucopyranoside (GSA-3), and β-D-glucopyranosylamine (GSA-1) were synthesized and concurrently tested with commercially available D-glucosamine (GSA-2) for antibacterial activity. Results obtained from this study showed a pronounced antagonist effect due to the position of amino groups of aminoglucose derivatives on the antibacterial activity. GSA-3 was the most active compound. At a concentration of 2 × 10 -4 mol mL -1, it delayed the growth of both bacteria with percentages of inhibition of 29 and 15% for L. innocua and S. typhimurium, respectively. At the same concentration the percentages of inhibition for other aminodeoxyglucoses varied between 5 and 18% and between 2 and 11% for L. innocua and S. typhimurium, respectively. All compounds were characterized by FTIR, 1H NMR, and 13C NMR spectroscopy.

Chemoenzymatic synthesis of glycosylated glucagon-like peptide 1: Effect of glycosylation on proteolytic resistance and in vivo blood glucose-lowering activity

Glucagon-like peptide 1 (7-36) amide (GLP-1) has been attracting considerable attention as a therapeutic agent for the treatment of type 2 diabetes. In this study, we applied a glycoengineering strategy to GLP-1 to improve its proteolytic stability and in vivo blood glucose-lowering activity. Glycosylated analogues with A/-acetylglucosamine (GlcNAc), A/-acetyllactosamine (LacNAc), and α2,6-sialyl N-acetyl-lactosamine (sialyl LacNAc) were prepared by chemoenzymatic approaches. We assessed the receptor binding affinity and cAMP production activity in vitro, the proteolytic resistance against dipeptidyl peptidase-IV (DPP-IV) and neutral endopeptidase (NEP) 24.11, and the blood glucose-lowering activity in diabetic db/db mice. Addition of sialyl LacNAc to GLP-1 greatly improved stability against DPP-IV and NEP 24.11 as compared to the native type. Also, the sialyl LacNAc moiety extended the blood glucose-lowering activity in vivo. Kinetic analysis of the degradation reactions suggested that the sialic acid component played an important role in decreasing the affinity of peptide to DPP-IV. In addition, the stability of GLP-1 against both DPP-IV and NEP24.11 incrementally improved with an increase in the content of sialyl LacNAc in the peptide. The di- and triglycosylated analogues with sialyl LacNAc showed greatly prolonged blood glucose-lowering activity of up to 5 h after administration (100 nmol/kg), although native GLP-1 showed only a brief duration. This study is the first attempt to thoroughly examine the effect of glycosylation on proteolytic resistance by using synthetic glycopeptides having homogeneous glycoforms. This information should be useful for the design of glycosylated analogues of other bioactive peptides as desirable pharmaceuticals.

Synthesis and biological evaluation of technetium-labeled d-glucose-MAG3 derivative as agent for tumor diagnosis

A d-glucose-MAG3 derivative was successfully synthesized and radiolabeled in high labeling yield. Biodistribution studies in Ehrlich tumor-bearing mice were performed. This compound showed high accumulation in tumor tissue with high tumor-to-muscle ratio and moderate tumor-to-blood ratio. Thus, d-glucose-MAG3 is a potential agent for tumor diagnosis.

Synthesis of neoglycoconjugates by the desulfurative rearrangement of allylic disulfides

(Chemical Equation Presented) Two series of neoglycosyl donors are prepared on the basis of connection of an allylic disulfide motif to the anomeric center via a simple O-glycosyl linkage or N-glycosyl amide unit. Conjugation of both sets of donors to cysteine in peptides is demonstrated through classical disulfide exchange followed by the phosphine-mediated desulfurative allylic rearrangement resulting in neoglycopeptides characterized by a simple thioether spacer. The conjugation reaction functions in the absence of protecting groups on both the neoglycosyl donor and peptide in aqueous media at room temperature.