3068-32-4Relevant academic research and scientific papers
Glycosylation chemistry promoted by iodine monobromide: Efficient synthesis of glycosyl bromides from thioglycosides, and O-glycosides from 'disarmed' thioglycosides and glycosyl bromides
Kartha, K. P. Ravindranathan,Field, Robert A.
, p. 8233 - 8236 (1997)
Iodine monobromide has been found to be an efficient reagent for the conversion of both 'armed' and 'disarmed' thioglycosides (-SMe, -SPr(i), - SPh) into glycosyl bromides. This reagent is compatible with most common protecting groups, and O-glycosidic linkages. The additional potency of I- Br, compared to iodine, as an iodonium ion source also permits the glycosylation of sugar alcohols by 'disarmed' glycosyl bromides and thioglycosides.
Synthesis of P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-α-D-rhamnopyranosyl-α-D-glucopyranosyl) diphosphate and P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl) diphosphate for the investigation of biosynthesis of O-antigenic polysaccharides in Pseudomonas aeruginosa and Escherichia coli O104
Torgov, Vladimir,Danilov, Leonid,Utkina, Natalia,Veselovsky, Vladimir,Brockhausen, Inka
, p. 19 - 25 (2017)
Two new phenoxyundecyl diphosphate sugars were synthesized for the first time: P1-(11-phenoxyundecyl)-P2- (2-acetamido-2-deoxy-3-O-α-D-rhamnopyranosyl-α-D-glucopyranosyl) diphosphate and P1-(11-phenoxyundecyl)-P2-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl) diphosphate to study the third step of biosynthesis of the repeating units of O-antigenic polysaccharides in Pseudomonas aeruginosa and E.coli O104 respectively.
Synthesis of glycoside derivatives of hydroxyanthraquinone with ability to dissolve and inhibit formation of crystals of calcium oxalate. Potential compounds in kidney stone therapy
Frackowiak, Anna,Skibiński, Przemys?aw,Gawe?, Wies?aw,Zaczyńska, Ewa,Czarny, Anna,Gancarz, Roman
, p. 1001 - 1007 (2010)
Synthesis of glycosyl derivatives of hydroxyanthraquinones (6-10) potentially useful for kidney stone therapy is presented. These compounds were analyzed as inhibitors of calcium oxalate crystals formation as well as substances with the ability of dissolving crystalline calcium oxalate. In addition, the effect of the compounds obtained on real kidney stones was analyzed by ex vivo tests. The tests on L929 and A545 cell lines have shown that the compounds obtained were not cytotoxic.
In Situ Preparation of β-D-1-O-Hydroxylamino Carbohydrate Polymers Mediated by Galactose Oxidase
Andreana, Peter R.,Xie, Wenhua,Cheng, Huai N.,Qiao, Lei,Murphy, Dennis J.,Gu, Qu-Ming,Wang, Peng G.
, p. 1863 - 1866 (2002)
(Equation Presented) Galactose oxidase produced a C-6 aldehyde in various terminal-containing galactose hydroxylamines for the simultaneous in situ generation of an A-B type condensation for the construction of unique oxime polymers. Molecular weights of the corresponding polymers were determined to be in the range of 4200-8900 g/mol, respectively. This indicates that approximately 20-25 sugar units were incorporated in these unique polymers.
Probing bacterial-toxin inhibition with synthetic glycopolymers prepared by tandem post-polymerization modification: Role of linker length and carbohydrate density
Richards, Sarah-Jane,Jones, Mathew W.,Hunaban, Mark,Haddleton, David M.,Gibson, Matthew I.
, p. 7812 - 7816 (2012)
Probing the depths: A tandem post-polymerization modification strategy was used to systematically probe the multivalent inhibition of a bacterial toxin as a function of linker length (see scheme), carbohydrate density, and glycopolymer chain length. Guided by structural-biology information, the binding-pocket depth of the toxin was probed and used as a means to specifically improve inhibition of the toxin by the glycopolymer. Copyright
Convenient synthesis of glycosylated hydroxylysine derivatives for use in solid-phase peptide synthesis
Malkar, Navdeep B.,Lauer-Fields, Janelle L.,Fields, Gregg B.
, p. 1137 - 1140 (2000)
δ-O-Glycosylated 9-fluorenylmethoxycarbonyl-hydroxylysine (Fmoc-Hyl) derivatives have been conveniently prepared by introduction of a β-D- galactopyranosyl group to copper-complexed Hyl[ε-tert-butyloxycarbonyl (Boc)] or Hyl[ε-allyloxycarbonyl (Aloc)], followed by decomposition of the copper complex and addition of an Fmoc group to the α-amino group. Fmoc- Hyl[ε-Boc,O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)] was used in the solid-phase synthesis of a type IV collagen derived sequence. (C) 2000 Elsevier Science Ltd.
N-Oxyamide-linked glycoglycerolipid coated AuNPs for receptor-targeting imaging and drug delivery
Chen, Na,Yu, Zhi-Hao,Zhou, Dan,Hu, Xi-Le,Zang, Yi,He, Xiao-Peng,Li, Jia,Xie, Juan
, p. 2284 - 2287 (2016)
The synthesis of a series of new N-oxyamide-linked glycoglycerolipids and their assembly with gold nanoparticles for receptor-targeting imaging and drug delivery are reported.
Application of Ugi reactions in synthesis of divalent neoglycoconjugates: Evidence that the sugars are presented in restricted conformation
Bradley, Helena,Fitzpatrick, Geraldine,Glass, W. Kenneth,Kunz, Horst,Murphy, Paul V.
, p. 2629 - 2632 (2001)
(Equation presented) The Ugi reaction has been used to prepare divalent galactose derivatives. NMR analysis shows that a divalent neoglycoconjugate, where the glycopeptides are bridged by a terephthaloyl group, is an 83:17 mixture of two conformers; the amide groups of the major isomer have E-anti conformations. The spatial relationship and the relative orientation of the sugars are restricted, which may have consequences for the recognition of this and related structures in biological systems.
Design, Synthesis, biological investigations and molecular interactions of triazole linked tacrine glycoconjugates as Acetylcholinesterase inhibitors with reduced hepatotoxicity
Ahmed, Ajaz,Bhagat, Kavita,Choudhary, Sushil,Kaur Gulati, Harmandeep,Kumar, Ajay,Kumar, Nitish,Mukherjee, Debaraj,Singh Bedi, Preet Mohinder,Singh, Atamjit,Singh, Harbinder,Vir Singh, Jatinder
, (2021/11/23)
Tacrine is a known Acetylcholinesterase (AChE) inhibitors having hepatotoxicity as main liability associated with it. The present study aims to reduce its hepatotoxicity by synthesizing tacrine linked triazole glycoconjugates via Huisgen's [3 + 2] cycloaddition of anomeric azides and terminal acetylenes derived from tacrine. A series of triazole based glycoconjugates containing both acetylated (A-1 to A-7) and free sugar hydroxyl groups (A-8 to A-14) at the amino position of tacrine were synthesized in good yield taking aid from molecular docking studies and evaluated for their in vitro AChE inhibition activity as well as hepatotoxicity. All the hybrids were found to be non-toxic on HePG2 cell line at 200 μM (100 % cell viability) as compared to tacrine (35 % cell viability) after 24 h of incubation period. Enzyme kinetic studies carried out for one of the potent hybrids in the series A-1 (IC50 0.4 μM) revealed its mixed inhibition approach. Thus, compound A-1 can be used as principle template to further explore the mechanism of action of different targets involved in Alzheimer's disease (AD) which stands as an adequate chemical probe to be launched in an AD drug discovery program.
Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents
Li, Xiao-San,Chen, Tang-Ji,Xu, Zhi-Peng,Long, Juan,He, Miao-Ying,Zhan, He-Hui,Zhuang, Hai-Cai,Wang, Qi-Lin,Liu, Li,Yang, Xue-Mei,Tang, Jin-Shan
, (2021/12/30)
In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.
