183875-35-6

Upstream product

• 171032-74-9 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-glucopyranose 
• 108-98-5 thiophenol 
• 56883-33-1 2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl acetate 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 530-26-7 D-Mannose 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 79733-39-4 1,3,4,6-tetra-O-acetyl-2-bromo-2-deoxy-α-D-mannopyranoside 
• 131087-35-9 phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 

Downstream Products

• 1228577-49-8 phenyl-3,4,6-tri-O-acetyl-2-amino-2-deoxy-1-thio-α-D-glucopyranoside 
• 277756-84-0 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-β-D-glucopyranoside 
• 220688-23-3 phenyl 2-azido-3,6-di-O-benzyl-2-deoxy-1-thio-α-D-glucopyranoside 
• 277756-85-1 phenyl 2-azido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside 

Relevant academic research and scientific papers

Conformational Lock of Glycosyl Donors Using Cyclic Carbamates

Axial rich glycosyl donors often display superior reactivity and stereoselectivity in glycosylations. In this study, a glucosamine glycosyl donor, locked in a 1C4 conformation by a six-membered carbamate ring, i.e. an oxazinone, is synthesized and studied. The 2N,4O carbamate is synthesized in one step from the corresponding azide. The glycosylation properties were studied by glycosylating different alcohols. Derivatives of the glycosyl donor were synthesized by introducing Ac, Troc, Ts, and Ms groups on the oxazinone nitrogen. The ring opening to give the glycoside in the 4C1 conformation was found to proceed smoothly using Zemplén conditions.

Improvement of the stereoselectivity of the glycosylation reaction with 2-azido-2-deoxy-1-thioglucoside donors

2-Azido-2-deoxy-1-thioglucoside donors with an electron withdrawing group at position 6 were employed to study the stereoselectivity of the glycosylation reaction with several acceptors, ranging from unhindered small primary alcohols to other sugars and s

Scalable Synthesis of Anomerically Pure Orthogonal-Protected GlcN3 and GalN3 from d -Glucosamine

An improved and scalable synthesis of orthogonally protected d-glucosamine and d-galactosamine building blocks from inexpensive d-glucosamine has been developed. The key reaction is an inversion/migration step providing access to a fully orthogonal protec

Design, synthesis and evaluation of cytotoxic properties of bisamino glucosylated antitumor ether lipids against cancer cells and cancer stem cells

Glycosylated antitumor ether lipids (GAELs) are a class of amphiphilic antitumor agents that kill cancer cells by a non-apoptotic pathway. Previous studies have shown that 2-amino-2-deoxy-d-gluco-based GAELs such as α-GLN and β-GLN show greatly improved antitumor activity against epithelial cancer cells and stem cells. To further optimize the bioactivity, we prepared a series of diamino-d-gluco-based GAELs and their analogs, and screened them against a panel of human epithelial cancer cell lines and cancer stem cells. Most of the new GAEL analogs are more potent than chlorambucil, cisplatin and salinomycin. The most potent bisamine-based GAEL analogs 1, 2, 4 and 8 showed 2- to 3-fold enhanced cytotoxicity against various cancer cell lines when compared to β-GLN, indicating that the addition of a second amino group enhances the cytotoxic effect. The effect of the most active dicationic GAELs 1 and 4 on cancer stem cells isolated from breast (BT-474) and prostate (DU-145) cell lines revealed that the two GAELs inhibited the formation of tumor spheres and resulted in >95% loss of viability of the cancer stem cells at 5 μM. Activity of GAEL 1 against BT-474 cancer stem cells is superior to that of salinomycin.

HEXOSE DERIVATIVES, PREPARATION AND USES THEREOF

A compound of formula I : or a salt thereof, wherein: R1 is -OC(H) (X) (CH2)nC(=O)OH; R2 is -OH, -N3, or -N (H) C (=O) CH3; or R1 and R2 together with the carbon atoms to which t

DI- AND TRI-CATIONIC GLYCOSYLATED ANTITUMOR ETHER LIPIDS, L-GUCOSYLATED GAELS AND RHAMNOSE-LINKED GAELS AS CYTOTOXIC AGENTS AGAINST EPITHELIAL CANCER CELLS AND CANCER STEM CELLS

Glycosylated Antitumor Ether Lipids (GAELs) kill cancer cells by a nonapoptotic pathway which is an attractive strategy to avoid resistance. To further optimize the antitumor effect, we prepared various analogs of di-, and tri-cationic GAEL analogs differing in the nature of the sugar (D-giucose or L-glucose), the anomeric linkage as well as position of the glycerolipid moiety. The di- and tri-cationic GAELs were synthesized and their in vitro anticancer properties were evaluated against drug resistant and aggressively growing cancer cell lines derived from human breast, prostate, pancreatic and ovarian cancers. The most potent dicationic GAEL analogs were also studied against cancer stem cells obtained from breast BT 474, prostate DU145 and ovarian A2780cp cell lines. Our results indicate that the number of positive charges, the position of the amino substituents and the nature of the sugar have significant effects on the anticancer activities of these compounds. The most active analog kill 50% of the cells at concentration range of 0.5-5μΜ and 90% of the cells at the concentration of 1-10μΜ depending on type of cancer cells.

Conformational changes associated with post-translational modifications of pro143 in Skp1 of dictyostelium -a dipeptide model system

Prolyl hydroxylation and subsequent glycosylation of the E3SCF ubiquitin ligase subunit Skp1 affects its conformation and its interaction with F-box proteins and, ultimately, O2-sensing in the organism. Taking a reductionist approach to understand the molecular basis for these effects, a series of end-capped Thr-Pro dipeptides was synthesized, tracking the sequential post-translational modifications that occur in the protein. The conformation of the pyrrolidine ring in each compound was gauged via coupling constants (3JHα,Hβ) and the electronegativity of the Cγ-substituents by chemical shifts (13C). The equilibrium between the cis-trans conformations about the central prolyl peptide bond was investigated by integration of signals corresponding to the two species in the 1H NMR spectra over a range of temperatures. These studies revealed an increasing preference for the trans-conformation in the order Pro a reduced rate for the trans-to-cis conversion and a significant increase in the cis-to-trans conversion upon hydroxylation of the proline residue in the dipeptide. NOE experiments suggest that the Thr side chain pushes the sugar away from the pyrrolidine ring. These effects, which depended on the presence of the N-terminal Thr residue, offer a mechanism to explain altered properties of the corresponding full-length proteins.

Synthesis and scalable conversion of L-iduronamides to heparin-related Di- and tetrasaccharides

A diastereomerically pure cyanohydrin, preparable on kilogram scale, is efficiently converted in one step into a novel L-iduronamide. A new regioselective acylation of this iduronamide and a new mild amide hydrolysis method mediated by amyl nitrite enable

Studies on the selectivity between nickel-catalyzed 1,2- cis -2-Amino glycosylation of hydroxyl groups of thioglycoside acceptors with C(2)-Substituted benzylidene N -Phenyl trifluoroacetimidates and intermolecular aglycon transfer of the sulfide group

The stereoselective synthesis of saccharide thioglycosides containing 1,2-cis-2-amino glycosidic linkages is challenging. In addition to the difficulties associated with achieving high α-selectivity in the formation of 1,2-cis-2-amino glycosidic bonds, th

Conjugates of plumbagin and phenyl-2-amino-1-thioglucoside inhibit MshB, a deacetylase involved in the biosynthesis of mycothiol

N-Acetylglucosaminylinositol (GlcNAc-Ins)-deacetylase (MshB) and mycothiol-S-conjugate amidase (Mca), structurally related amidases present in mycobacteria and other Actinomycetes, are involved in the biosynthesis of mycothiol and in the detoxification of