81972-19-2Relevant academic research and scientific papers
Understanding multivalent effects in glycosidase inhibition using: C -glycoside click clusters as molecular probes
Stauffert, Fabien,Bodlenner, Anne,Nguyet Trinh, Thi Minh,García-Moreno, M. Isabel,Ortiz Mellet, Carmen,Nierengarten, Jean-Fran?ois,Compain, Philippe
, p. 7421 - 7430 (2016)
The synthesis of the first examples of multivalent C-glycosides based on C60-fullerene or β-cyclodextrin cores by way of Cu(i)-catalyzed azide-alkyne cycloadditions is reported. These compounds were designed as molecular probes to understand the mechanisms underlying the outstanding multivalent effects observed in glycosidase inhibition. The inhibition results obtained support a multivalent-binding model based on two scenarios both involving nonspecific interactions and varying by the presence or the absence of active site specific interactions. The magnitude of the multivalent effect obtained depends on the identity of the glycosidase involved and more specifically on the accessibility of its catalytic active site. Large inhibitory multivalent effects can be obtained when both glycosidase active sites and non-catalytic sites at the protein surface are involved in binding events. On the other hand, nonspecific interactions alone are not sufficient to achieve relative affinity enhancements exceeding a simple statistical effect (i.e., a relative inhibition potency not better than one on a valence-corrected basis).
Synthesis of a DOTA-C-glyco bifunctional chelating agent and preliminaryin vitroandin vivostudy of [68Ga]Ga-DOTA-C-glyco-RGD
Mangin, Floriane,Collet, Charlotte,Jouan-Hureaux, Valérie,Maskali, Fatiha,Roeder, Emilie,Pierson, Julien,Selmeczi, Katalin,Marie, Pierre-Yves,Boura, Cédric,Pellegrini-Mo?se, Nadia,Lamandé-Langle, Sandrine
, p. 7672 - 7681 (2021/02/26)
The design of bifunctional chelating agents (BFCA) allowing straightforward radiometal labelling of biomolecules is a current challenge. We report herein the development of a bifunctional chelating agent based on a DOTA chelator linked to aC-glycosyl compound, taking advantage of the robustness and hydrophilicity of this type of carbohydrate derivative. This new BFCA was coupled with success by CuAAC with c(RGDfK) for αvβ3integrin targeting. As attested byin vitroevaluation, the conjugate DOTA-C-glyco-c(RGDfC) demonstrated high affinity for αvβ3integrins (IC50of 42 nM). [68Ga]Ga-DOTA-C-glyco-c(RGDfK) was radiosynthesized straightforwardly and showed high hydrophilic property (log?D7.4= ?3.71) andin vitrostability (>120 min). Preliminaryin vivoPET study of U87MG engrafted mice gave evidence of an interesting tumor-to-non-target area ratio. All these data indicate that [68Ga]Ga-DOTA-C-glyco-c(RGDfK) allows monitoring of αvβ3expression and could thus be used for cancer diagnosis. The DOTA-C-glycoside BFCA reported here could also be used with various ligands and chelating other (radio)metals opening a broad scope of applications in imaging modalities and therapy.
Mild cu(Otf)2-mediated C-glycosylation with chelation-assisted picolinate as a leaving group
Tang, Weiping,Ye, Wenjing,Stevens, Christopher M.,Wen, Peng,Simmons, Christopher J.
, p. 16218 - 16225 (2021/01/19)
C-Glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were developed. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)2 and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corresponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.
C -Glycosylation enabled by N -(glycosyloxy)acetamides
Li, Bo-Han,Li, Tian,Liu, Meng,Liu, Miao,Wu, Xia,Xiong, De-Cai,Ye, Xin-Shan
supporting information, p. 3043 - 3046 (2020/05/08)
The C-glycosylation of C-nucleophiles including allyltrimethylsilane, silyl enol ethers and phenols with N-(glycosyloxy)acetamides as glycosyl donors has been realized. This protocol provides a convenient and practical route for the synthesis of alkyl C-glycosides and aryl 2-deoxy-β-C-glycosides under mild reaction conditions.
Synthesis and revised stereochemical assignment of C-allyl glucopyranosides and derivatives
Petry, Nicolas,Vucko, Timothé,Collet, Charlotte,Lamandé-Langle, Sandrine,Pellegrini-Mo?se, Nadia,Chrétien, Fran?oise
supporting information, p. 61 - 64 (2017/04/19)
α- and β-C-allylglucopyranosides and hydroxy-, bromo- and azido-derivatives were prepared through allylation at C-1 of methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside or 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose and subsequent chemical modificatio
GLUCOSE-RESPONSIVE INSULIN CONJUGATES
-
Page/Page column 139; 147, (2016/10/31)
Insulin conjugates comprising an insulin analog molecule covalently attached to at least one bi-dentate linker having two arms, each arm independently attached to a ligand comprising a saccharide and wherein the saccharide for at least one ligand of the linker is fucose are disclosed. The insulin conjugates 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 such as Con A.
Gold-catalyzed diastereoselective synthesis of 2,6-trans-disubstituted tetrahydropyran derivatives: application for the synthesis of the C1-C13 fragment of bistramide A and B
Padhi, Birakishore,Reddy, D. Srinivas,Mohapatra, Debendra K.
, p. 96758 - 96768 (2015/11/24)
An efficient gold(iii)-catalyzed general method for the diastereoselective allylation of six-membered cyclic hemiacetals at room temperature is developed. The present protocol is operationally simple with good functional group tolerance, thus providing easy access to various multifunctionalized 2,6-trans-disubstituted tetrahydropyrans. Since an allyl moiety is readily introduced, the developed strategy is highly versatile and has great potential for further functional group manipulation. Furthermore, a diastereoselective synthesis of the C1-C13 fragment of bistramide A and B has been described highlighting this methodology.
Gold-catalysed glycosylation reaction using an easily accessible leaving group
Koppolu, Srinivasa Rao,Niddana, Ramana,Balamurugan, Rengarajan
, p. 5094 - 5097 (2015/05/13)
Gold(iii)-catalysed glycosylation reaction has been developed by employing a new and easily accessible leaving group synthesized from ethyl cyanoacetate. Several nucleophiles like alcohols, thiols, allyltrimethylsilane, trimethylsilyl azide and triethylsilane have been reacted to make the corresponding glycosides in good yields and with marginal to excellent α-selectivity. This journal is
GLUCOSE-RESPONSIVE INSULIN CONJUGATES
-
Paragraph 0504; 0526, (2015/04/21)
Insulin conjugates comprising an insulin molecule covalently attached to at least one bi-dentate linker having two arms, each arm independently attached to a ligand comprising a saccharide and wherein the saccharide for at least one ligand of the linker is fucose are disclosed. The insulin conjugates 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 such as Con A.
Adaptable synthesis of C-glycosidic multivalent carbohydrates and succinamide-linked derivatization
Miller, Gavin J.,Gardiner, John M.
supporting information; experimental part, p. 5262 - 5265 (2011/02/24)
A modular approach to the synthesis of trivalent C-glycosidic carbohydrates is described. The approach is illustrated employing carboxylate-terminated C-glycosidic d-mannose, d-glucose, and d-galactose derivatives with different length C1-linked spacer un
