β-D-(1,2)-mannotriose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-(1,2)-mannotriose
• 英文别名: beta-D-mannopyranosyl-(1->2)-beta-D-mannopyranosyl-(1->2)-D-mannopyranose；(3S,4S,5S,6R)-3-[(2S,3S,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,4,5-triol
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: UQBIAGWOJDEOMN-WHFFQBEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  269
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  β-D-(1,2)-mannotriose 在 sodium azide 、 2-chloro-1,3-dimethylimidazolinium chloride 、 N,N-二异丙基乙胺 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  β-1,2-寡甘露聚糖磷酸化酶介导的潜在寡糖疫苗候选物的合成

  摘要：

  将 β-(1,2)-甘露聚糖抗原掺入用于免疫研究的候选疫苗中，表明针对 β-(1,2)-甘露三糖抗原产生的抗体可以预防播散性念珠菌病。 直到最近，β-(1,2)-甘露聚糖只能通过从微生物培养物中分离或通过涉及保护基操作的冗长合成策略获得。两种 β-(1,2)-甘露糖苷磷酸化酶 Teth514_1788 和 Teth514_1789 的发现使得能够有效地获取这些化合物。在这项工作中，Teth514_1788 用于生成 β-(1,2)-甘露聚糖抗原、三糖和四糖，在还原端装饰有缀合系链，适合结合到载体上用于新型疫苗候选人，这里通过三糖与 BSA 的结合来说明。

  DOI：

  10.1016/j.carres.2023.108807

文献信息

• The GH130 Family of Mannoside Phosphorylases Contains Glycoside Hydrolases That Target β-1,2-Mannosidic Linkages in Candida Mannan
  作者：Fiona Cuskin、Arnaud Baslé、Simon Ladevèze、Alison M. Day、Harry J. Gilbert、Gideon J. Davies、Gabrielle Potocki-Véronèse、Elisabeth C. Lowe

  DOI：10.1074/jbc.m115.681460

  日期：2015.10

  The depolymerization of complex glycans is an important biological process that is of considerable interest to environmentally relevant industries. beta-Mannose is a major component of plant structural polysaccharides and eukaryotic N-glycans. These linkages are primarily cleaved by glycoside hydrolases, although recently, a family of glycoside phosphorylases, GH130, have also been shown to target beta-1,2- and beta-1,4-mannosidic linkages. In these phosphorylases, bond cleavage was mediated by a single displacement reaction in which phosphate functions as the catalytic nucleophile. A cohort of GH130 enzymes, however, lack the conserved basic residues that bind the phosphate nucleophile, and it was proposed that these enzymes function as glycoside hydrolases. Here we show that two Bacteroides enzymes, BT3780 and BACOVA_03624, which lack the phosphate binding residues, are indeed beta-mannosidases that hydrolyze beta-1,2-mannosidic linkages through an inverting mechanism. Because the genes encoding these enzymes are located in genetic loci that orchestrate the depolymerization of yeast alpha-mannans, it is likely that the two enzymes target the beta-1,2-mannose residues that cap the glycan produced by Candida albicans. The crystal structure of BT3780 in complex with mannose bound in the -1 and +1 subsites showed that a pair of glutamates, Glu(227) and Glu(268), hydrogen bond to O-1 of alpha-mannose, and either of these residues may function as the catalytic base. The candidate catalytic acid and the other residues that interact with the active site mannose are conserved in both GH130 mannoside phosphorylases and beta-1,2-mannosidases. Functional phylogeny identified a conserved lysine, Lys(199) in BT3780, as a key specificity determinant for beta-1,2-mannosidic linkages.
• An inverting β-1,2-mannosidase belonging to glycoside hydrolase family 130 from<i>Dyadobacter fermentans</i>
  作者：Takanori Nihira、Kazuhiro Chiku、Erika Suzuki、Mamoru Nishimoto、Shinya Fushinobu、Motomitsu Kitaoka、Ken'ichi Ohtsubo、Hiroyuki Nakai

  DOI：10.1016/j.febslet.2015.10.008

  日期：2015.11.30

  The glycoside hydrolase family (GH) 130 is composed of inverting phosphorylases that catalyze reversible phosphorolysis of β‐d‐mannosides. Here we report a glycoside hydrolase as a new member of GH130. Dfer_3176 from Dyadobacter fermentans showed no synthetic activity using α‐d‐mannose 1‐phosphate but it released α‐d‐mannose from β‐1,2‐mannooligosaccharides with an inversion of the anomeric configuration, indicating that Dfer_3176 is a β‐1,2‐mannosidase. Mutational analysis indicated that two glutamic acid residues are critical for the hydrolysis of β‐1,2‐mannotriose. The two residues are not conserved among GH130 phosphorylases and are predicted to assist the nucleophilic attack of a water molecule in the hydrolysis of the β‐d‐mannosidic bond.
• β-1,2-Oligomannan phosphorylase-mediated synthesis of potential oligosaccharide vaccine candidates
  作者：Sanaz Ahmadipour、Rebecca Winsbury、Dominic Köhler、Giulia Pergolizzi、Sergey A. Nepogodiev、Simona Chessa、Simone Dedola、Meng Wang、Josef Voglmeir、Robert A. Field

  DOI：10.1016/j.carres.2023.108807

  日期：2023.6

  β-(1,2)-Mannan antigens incorporated into vaccines candidates for immunization studies, showed that antibodies raised against β-(1,2)-mannotriose antigens can protect against disseminated candidiasis. Until recently, β-(1,2)- mannans could only be obtained by isolation from microbial cultures, or by lengthy synthetic strategies involving protecting group manipulation. The discovery of two β-(1,2)-mannoside

  将 β-(1,2)-甘露聚糖抗原掺入用于免疫研究的候选疫苗中，表明针对 β-(1,2)-甘露三糖抗原产生的抗体可以预防播散性念珠菌病。 直到最近，β-(1,2)-甘露聚糖只能通过从微生物培养物中分离或通过涉及保护基操作的冗长合成策略获得。两种 β-(1,2)-甘露糖苷磷酸化酶 Teth514_1788 和 Teth514_1789 的发现使得能够有效地获取这些化合物。在这项工作中，Teth514_1788 用于生成 β-(1,2)-甘露聚糖抗原、三糖和四糖，在还原端装饰有缀合系链，适合结合到载体上用于新型疫苗候选人，这里通过三糖与 BSA 的结合来说明。