14365-73-2

Usage

Uses

Used in Pharmaceutical Industry:
1-Amino-1-deoxy-2,3,4-triacetate β-D-Glucopyranuronic Acid Methyl Ester is used as a pharmaceutical intermediate for the development of drugs targeting specific biological interactions. Its unique structure allows it to be a potential candidate in the design and synthesis of novel therapeutic agents.
Used in Biological Studies:
1-Amino-1-deoxy-2,3,4-triacetate β-D-Glucopyranuronic Acid Methyl Ester is used as a research tool in biological studies for the inhibitor identification of fibroblast growth factor (FGF-2) binding to heparin and endothelial cells. Its specific structural features enable it to interfere with the binding process, providing valuable insights into the molecular mechanisms underlying FGF-2 signaling and its role in various biological processes.

Upstream product

• 67776-38-9 2,3,4-tri-O-acetyl-1-azido-1-deoxy-β-D-glucopyranuronic acid methyl ester 
• 325811-01-6 (S,S)-(-)-1,2-di(p-chlorophenyl)ethane-1,2-diol 
• 63-29-6 D-glucurono-6,3-lactone 
• 3082-96-0 methyl 1,2,3,4-tetra-O-acetyl-α,β-D-glucopyranosyluronate 
• 82228-14-6 methyl D-glucopyranuronate 
• 7355-18-2 (2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 57820-69-6 (3R,4S,5S,6S)-2-bromo-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 487-44-5 D-(+)-glucuronic acid γ-lactone 
• 6919-98-8 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-β-D-glucopyranuronic acid methy ester 
• 21085-72-3 1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester 

Downstream Products

• 183742-71-4 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-((2S,3R)-2-benzyloxycarbonylamino-3-tert-butoxy-butyrylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 201414-05-3 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-[(2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoylamino]-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 500340-02-3 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,5-dimethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 500339-93-5 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(2-biphenyl-4-yl-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 500339-96-8 7-methyl 1-deoxy-1-{[(2,4-dichlorophenoxy)acethyl]amino}-2,3,4-tri-O-acetyl-β-D-glucopyranuronate 
• 755023-81-5 N-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl)amide-isophthalamic acid 
• 500340-01-2 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 500340-00-1 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4-difluoro-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 500339-53-7 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(4-oxo-4-phenyl-butyrylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 500340-03-4 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3,4,5-trimethoxy-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 755023-88-2 C₄₇H₅₆N₄O₂₂ 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II

A series of new carbohydrate-based sulphonamide derivatives were designed, synthesised by employing the so-call ‘sugar-tail’ approach. The compounds were evaluated in vitro against a panel of CAs. Compared to their parent compound p-sulfamoylbenzoic acid, these compounds showed nearly 100-fold improvement in their binding affinities against hCA II in vitro. All of compounds showed great water solubility and the pH value of their water solutions of compounds is 7.0. Such properties are advantageous to make them much less irritating to the eye when applied topical glaucomatous drugs, compared to the relatively highly acidic dorzolamide preparations (pH 5.5). Notably, compounds 7d, 7 g, 7 h demonstrated to topically lower intraocular pressure (IOP) in glaucomatous animals better than brinzolamide when applied as a 1% solution directly into the eye. Low cytotoxicity on human cornea epithelial cell was observed in the tested concentrations by the MTT assay.

Synthesis of N-(β-d-glycuronopyranosyl)alkanamides and 1-(β-d-glycuronopyranosyl)-4-phenyl-[1,2,3]-triazoles as N-glycoprotein linkage region analogs: Examination of the effect of C5 substituent on the N-glycosidic torsion (ΦN) based on X-ray c

The torsion angle around the N-glycoprotein linkage region (GlcNAc-Asn) is an important factor for presenting sugar on the cell surface which is crucial for many biological processes. Earlier studies using model and analogs showed that this important tors

DIFFERENTIATION MODULATING AGENTS AND USES THEREFOR

This invention discloses methods and agents for modulating the differentiation potential and/or proliferation of preadipocytes. More particularly, the present invention discloses methods and agents for modulating a fibroblast growth factor (FGF) signalling pathway, especially the FGF-1 or FGF-2 signalling pathway, for treating or preventing adiposity-related conditions including, but not limited to, obesity, lipoma and lipomatosis.

Synthesis of a glucuronic acid and glucose conjugate library and evaluation of effects on endothelial cell growth

Compounds that alter endothelial cell growth are of interest in the development of angiogenesis modulators. A structurally diverse series of saccharide derivatives (glycosylamide conjugates) have been synthesized and evaluated for their effects on bovine

Development of carbohydrate-based scaffolds for restricted presentation of recognition groups. Extension to divalent ligands and implications for the structure of dimerized receptors

The solution structure of glycosyl amides has been studied by using NMR. A strong preference is displayed by tertiary aromatic glycosyl amides for E-anti structures in contrast with secondary aromatic glycosyl amides where Z-anti structures predominate. The structural diversity displayed by these classes of molecules would seem to be important as the directional properties of the aromatic ring, or groups attached to the aromatic ring, would be determined by choosing to have either a secondary or tertiary amide at the anomeric center and could be considered when designing bioactive molecules with carbohydrate scaffolds. The structural analysis was also carried out for related divalent secondary and tertiary glycosyl amides and these compounds display preferences similar to that of the monovalent compounds. The constrained divalent compounds have potential for promoting formation of clusters that will have restricted structure and thus have potential for novel studies of mechanisms of action of multivalent ligands. Possible applications of such compounds would be as scaffolds for the design and synthesis of ligands that will facilitate protein - protein or other receptor - receptor interactions. The affinity of restricted divalent (or higher order) ligands, designed to bind to proteins that recognize carbohydrates which would facilitate clustering and concomitantly promote protein - protein interactions, may be significantly higher than monovalent counterparts or multivalent ligands without these properties. This may be useful as a new approach in the development of therapeutics based on carbohydrates.

Rapid access to uronic acid-based mimetics of Kdn2en from D-glucurono-6,3-lactone

A concise route to novel mimetics of Kdn2en, based on Δ4-uronic acids, from D-glucurono-6,3-lactone is presented. Uronic acid-based mimetics in which an aliphatic ether (O-glycoside), a thioether (S-glycoside), or acetamide takes the place of the natural C-6 glycerol sidechain of the sialic acid were synthesized from the key intermediate, methyl 2,3,4-tri-O-acetyl-α-D-glucopyranosyluronate bromide. (C) 2000 Elsevier Science Ltd.

N-linked glycoside/glucuronide conjugates of retinoids: Acitretin

Glucuronide conjugates of retinoids have been found to be active metabolites of the parent molecules. However, O-acylglucuronide retinoids are liable to hydrolysis and retinoid ring oxidation. We have prepared stable N-linked glycosides of acitretin in efforts to overcome these problems. The synthesis and preliminary biological studies of the analogs are reported.

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.