5432-32-6Relevant articles and documents
Methyl tetra-O-acetyl-α-D-glucopyranuronate: crystal structure and influence on the crystallisation of the β anomer
Hayes, John A.,Eccles, Kevin S.,Lawrence, Simon E.,Moynihan, Humphrey A.
, p. 35 - 39 (2016)
Methyl tetra-O-acetyl-β-D-glucopyranuronate (1) and methyl tetra-O-acetyl-α-D-glucopyranuronate (3) were isolated as crystalline solids and their crystal structures were obtained. That of the β anomer (1) was the same as that reported by Root et?al., while anomer (3) was found to crystallise in the orthorhombic space group P212121with two independent molecules in the asymmetric unit. No other crystal forms were found for either compound upon recrystallisation from a range of solvents. The α anomer (3) was found to be an impurity in initially precipitated batches of β-anomer (1) in quantities a crystallographic direction in the absence of the α impurity, while the presence of the α anomer (3) enhanced this elongation.
Crystal structure of methyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate
Root, Yuriko Y.,Wagner, Timothy R.,Norris, Peter
, p. 2343 - 2346 (2002)
The identity of the crystalline product formed by the acetylation of a mixture of methyl α- and β-D-glucopyranuronates has been confirmed as being methyl 1,2,3,4-tetra-O-acetyl-β-D-glucopyranuronate (3), which agrees with the assignment from 1H NMR. The absolute configuration of compound 3 was assigned to agree with the known chirality of the precursor sugar, D-glucono-6,3-lactone.
Potent and Prolonged Innate Immune Activation by Enzyme-Responsive Imidazoquinoline TLR7/8 Agonist Prodrug Vesicles
Wang, Bi,Van Herck, Simon,Chen, Yong,Bai, Xiangyang,Zhong, Zifu,Deswarte, Kim,Lambrecht, Bart N.,Sanders, Niek N.,Lienenklaus, Stefan,Scheeren, Hans W.,David, Sunil A.,Kiessling, Fabian,Lammers, Twan,De Geest, Bruno G.,Shi, Yang
supporting information, p. 12133 - 12139 (2020/08/06)
Synthetic immune-stimulatory drugs such as agonists of the Toll-like receptors (TLR) 7/8 are potent activators of antigen-presenting cells (APCs), however, they also induce severe side effects due to leakage from the site of injection into systemic circulation. Here, we report on the design and synthesis of an amphiphilic polymer-prodrug conjugate of an imidazoquinoline TLR7/8 agonist that in aqueous medium forms vesicular structures of 200 nm. The conjugate contains an endosomal enzyme-responsive linker enabling degradation of the vesicles and release of the TLR7/8 agonist in native form after endocytosis, which results in high in vitro TLR agonist activity. In a mouse model, locally administered vesicles provoke significantly more potent and long-lasting immune stimulation in terms of interferon expression at the injection site and in draining lymphoid tissue compared to a nonamphiphilic control and the native TLR agonist. Moreover, the vesicles induce robust activation of dendritic cells in the draining lymph node in vivo.
A combinatorial approach towards the synthesis of non-hydrolysable triazole-iduronic acid hybrid inhibitors of human α-l-iduronidase: Discovery of enzyme stabilizers for the potential treatment of MPSI
Cheng, Wei-Chieh,Lin, Cheng-Kun,Li, Huang-Yi,Chang, Yu-Chien,Lu, Sheng-Jhih,Chen, Yu-Shin,Chang, Shih-Ying
supporting information, p. 2647 - 2650 (2018/03/21)
Preparation of substituent-diverse, triazole-iduronic acid hybrid molecules by click reaction of an azido iduronic acid derivative with randomly chosen alkynes is described. Library members were screened for their ability to inhibit α-l-iduronidase, and hit molecules and analogues were then investigated for their ability to stabilize rh-α-IDUA in a thermal denaturation study. This work resulted in the discovery of the first small molecules that can be used to stabilize exogenous rh-α-IDUA protein in vitro.