183901-63-5Relevant articles and documents
Oligomannoside mimetics by glycosylation of 'octopus glycosides' and their investigation as inhibitors of type 1 fimbriae-mediated adhesion of Escherichia coli
Dubber, Michael,Sperling, Oliver,Lindhorst, Thisbe K.
, p. 3901 - 3912 (2006)
The glycocalyx of eukaryotic cells is composed of glycoconjugates, which carry highly complex oligosaccharide portions. To elucidate the biological role and function of the glycocalyx in cell-cell communication and cellular adhesion processes, glycomimeti
New lipophilic glycomimetic DC-SIGN ligands: Stereoselective synthesis and SPR-based binding inhibition assays
Di Pietro, Sebastiano,Bordoni, Vittorio,Iacopini, Dalila,Achilli, Silvia,Pineschi, Mauro,Thépaut, Michel,Fieschi, Franck,Crotti, Paolo,Di Bussolo, Valeria
, (2021)
The design and synthesis of efficient ligands for DC-SIGN is a topic of high interest, because this C-type lectin has been implicated in the early stages of many infection processes. DC-SIGN membrane-protein presents four carbohydrate-binding domains (CRD) that specifically recognize mannose and fucose. Therefore, antagonists of minimal disaccharide epitope Manα(1,2)Man, represent potentially interesting antibacterial and antiviral agents. In the recent past, we were able to develop efficient antagonists, mimics of the natural moiety, characterized by the presence of a real D-carbamannose unit which confers greater stability to enzymatic breakdown than the corresponding natural disaccharide ligand. Herein, we present the challenging stereoselective synthesis of four new amino or azide glycomimetic DC-SIGN antagonists with attractive orthogonal lipophilic substituents in C(3), C(4) or C(6) positions of the real carba unit, which were expected to establish crucial interactions with lipophilic areas of DC-SIGN CRD. The activity of the new ligands was evaluated by SPR binding inhibition assays. The interesting results obtained, allow to acquire important information about the influence of the lipophilic substituents present in specific positions of the carba scaffold. Furthermore, C(6) benzyl C(4) tosylamide pseudodisaccharide displayed a good affinity for DC-SIGN with a more favorable IC50 value than those of the previously described real carba-analogues. This study provides valuable knowledge for the implementation of further structural modifications towards improved inhibitors.
Synthesis of Carbohydrate-Centered Oligosaccharide Mimetics Equipped with a Functionalized Tether
Dubber, Michael,Lindhorst, Thisbe K.
, p. 5275 - 5281 (2000)
Synthetic glycoclusters have gained substantial attention as mimetics of multivalent glycoconjugates. For their proposed glycobiological applications, it is advantageous to incorporate a functionalized tether into the clusters, which allows coupling to so
Synthesis of a Glycosylphosphatidylinositol (GPI) Fragment as a Potential Substrate for Mannoprotein Transglycosidases
Belz, Tyson F.,Williams, Spencer J.
, p. 2053 - 2058 (2021/08/31)
A glycophosphatidylinositol tetrasaccharide fragment was synthesized to mimic the core features of primary model, that of Saccharomyces cerevisiae. The salient feature of this approach is centered on the quick access to various α-1,2- and α-1,6-mannosyl a
Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides
Das, Anupama,Jayaraman, Narayanaswamy
, p. 9318 - 9325 (2021/11/13)
The allylic bromination of allyl glycosides is conducted using NBS/AIBN reagents in (EtO)2CO and PhCF3 solutions, without using CCl4 as a solvent. The activated mixed halo-allyl glycosides led to glycosylations, mediated by a triflate, in a latent-active
GLUCOSE-RESPONSIVE INSULIN CONJUGATES
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, (2021/02/05)
Glucose-responsive insulin conjugates that contain one or more trisaccharides are provided. Such insulin conjugates may display a pharmacokinetic (PK) and/or pharmacodynamic (PD) profile that is responsive to the systemic concentrations of a saccharide such as glucose or alpha-methylmannose, even when administered to a subject in need thereof in the absence of an exogenous multivalent saccharide-binding molecule.
36 branchings honeydews five sugar six sugar-to methoxyphenyl glycoside and its preparation method and application
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Paragraph 0070-0072, (2017/09/19)
The invention provides a 3,6-branched mannopentaose and hexaose on methoxy phenyl glycoside and a preparation method and an application thereof. A structural formula is shown in a formula I or a formula II; a compound can be used for preparing anti-HIV me
The dehydroepiandrosterone and dehydroepiandrosterone alkone glycosylation derivative and its preparation method and application
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Paragraph 0041; 0050; 0051, (2017/04/28)
The invention discloses epiandrosterone glycosylation derivatives and dehydrogenated epiandrosterone glycosylation derivatives, and a preparation method thereof. The preparation method comprises the following steps: respectively carrying out coupling reac
3 - monosaccharide acid oxygen glucoside oleanolic alkane type and wusu alkane triterpene saponin derivative and its preparation method and application
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Paragraph 0035; 0039; 0113, (2017/08/25)
The invention discloses a 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative. The derivative has a structural formula as shown in the specification, wherein R4 is one of H atom, alkyl containing 1-10 carbons, alkyl
Cross metathesis assisted solid-phase synthesis of glycopeptoids
Khan, Sharaf Nawaz,Kim, Arim,Grubbs, Robert H.,Kwon, Yong-Uk
, p. 2952 - 2955 (2012/07/30)
A solid-phase synthesis of glycopeptoids was explored through olefin cross metathesis (CM). Peptoids and sugar derivatives with appropriate olefin moieties were coupled in the presence of an olefin metathesis catalyst to afford glycopeptoids in good yield