α-D-glucopyranosyl-(1-3)-D-mannopyranose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-D-glucopyranosyl-(1-3)-D-mannopyranose
• 英文别名: alpha-D-glucosyl-(1->3)-D-mannopyranose；(3S,4S,5R,6R)-6-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2,3,5-triol
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: QIGJYVCQYDKYDW-WVUQMAKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  190
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  氯 2,3,4,6-四-O-苄基-|á-D-吡喃葡萄糖苷 在 10% palladium on active carbon 2,4,6-三甲基吡啶 、 氢气 、 silver trifluoromethanesulfonate 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 3.0h， 生成 α-D-glucopyranosyl-(1-3)-D-mannopyranose
  参考文献：
  名称：

  A Synthetic Approach to the Glycan Chain of High Mannose Type N-Glycoprotein

  摘要：

  The syntheses of alpha-D-glucopyranose-(1-->3)-D-mannopyranose, methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranoside and methyl alpha-D-glucopyranose-(1-->3)-alpha-D-mannopyranose-( 1--> 2)-alpha-D-mannopyranoside are reported. High stereoselectivity was observed during the coupling of glucose and mannose residues by the use of glucosyl trichloroacetimidate as donor.

  DOI：

  10.1080/07328309808001894

文献信息

• The high mannose glycans from bovine ribonuclease B isomer characterization by ion trap MS
  作者：Justin M. Prien、David J. Ashline、Anthony J. Lapadula、Hailong Zhang、Vernon N. Reinhold

  DOI：10.1016/j.jasms.2008.11.012

  日期：2009.4.1

  Thirteen high mannose isomers have been structurally characterized within three glycomers, Man5GlcNAc2, Man7GlcNAc2, and Man8GlcNAc2 released from bovine ribonuclease B, six previously unreported. The study was carried out with a single ion trap instrument involving no chromatography. Three previously characterized isomers from Man7 and Man8 (three each) have been identified plus one unreported Man7 isomer. Incomplete α-glucosidase activity on the Man6 and Man7 glycoproteins appears to account for two additional isomeric structures. The preeminence of ion traps for detail analysis was further demonstrated by resolving three new isomers within the Man5 glycomer summing to the six previously unreported structures in this glycoprotein. All reported structures represent a distribution of Golgi processing remnants that fall within the Man9GlcNAc2 footprint. Topologies were defined by ion compositions along a disassembly pathway while linkage and branching were aided by spectral identity in a small oligomer fragment library. Isomers from this glycoprotein appear to represent a distribution of Golgi processing remnants, and an alphanumeric classification scheme has been devised to identify all products. Although numerous analytical strategies have been introduced to identify selected components of structure, it has been the continued focus of this and previous reports to only build upon protocols that can be integrated into a high throughput strategy consistent with automation. Duplication of these and results from comparable standards could bring an important analytical focus to carbohydrate sequencing that is greatly lacking.

  在三种糖基化物Man5GlcNAc2、Man7GlcNAc2和Man8GlcNAc2（从牛核糖核酸酶B中释放）中，对13种高甘露糖异构体的结构进行了表征，其中6种是以前未报告过的。该研究使用一台单离子阱仪器进行，无需色谱分析。已鉴定出三种以前表征过的Man7和Man8异构体（各三种），以及一种未报告过的Man7异构体。Man6和Man7糖蛋白上的不完全α-葡萄糖苷酶活性似乎解释了另外两种异构体结构。通过解析Man5糖基化物中的三种新异构体，进一步证明了离子阱在细节分析方面的卓越性，这三种新异构体与该糖蛋白中以前未报告过的六种结构相加。所有已报告的结构都代表了高尔基加工残基的分布，这些残基属于Man9GlcNAc2足迹。通过沿分解路径的离子组成来定义拓扑结构，而通过小寡聚物片段库中的光谱特征来确定连接和分支。该糖蛋白的异构体似乎代表了高尔基加工残基的分布，已设计了一种字母数字分类方案来识别所有产物。尽管已经引入了许多分析策略来识别结构中的选定成分，但本报告和以前报告的重点仍然是仅基于可集成
• Intact α-1,2-endomannosidase is a typical type II membrane protein
  作者：Stephen R. Hamilton、Huijuan Li、Harry Wischnewski、Anita Prasad、Joanna S. Kerley-Hamilton、Teresa Mitchell、Amelia J. Walling、Robert C. Davidson、Stefan Wildt、Tillman U. Gerngross

  DOI：10.1093/glycob/cwi045

  日期：2005.6.1

  Rat endomannosidase is a glycosidic enzyme that catalyzes the cleavage of di-, tri-, or tetrasaccharides (Glc1–3Man), from N-glycosylation intermediates with terminal glucose residues. To date it is the only characterized member of this class of endomannosidic enzymes. Although this protein has been demonstrated to localize to the Golgi lumenal membrane, the mechanism by which this occurs has not yet been determined. Using the rat endomannosidase sequence, we identified three homologs, one each in the human, mouse, and rat genomes. Alignment of the four encoded protein sequences demonstrated that the newly identified sequences are highly conserved but differed significantly at the N-terminus from the previously reported protein. In this study we have cloned two novel endomannosidase sequences from rat and human cDNA libraries, but were unable to amplify the open reading frame of the previously reported rat sequence. Analysis of the rat genome confirmed that the 59- and 39-termini of the previously reported sequence were in fact located on different chromosomes. This, in combination with our inability to amplify the previously reported sequence, indicated that the N-terminus of the rat endomannosidase sequence previously published was likely in error (a cloning artifact), and that the sequences reported in the current study encode the intact proteins. Furthermore, unlike the previous sequence, the three ORFs identified in this study encode proteins containing a single N-terminal transmembrane domain. Here we demonstrate that this region is responsible for Golgi localization and in doing so confirm that endomannosidase is a type II membrane protein, like the majority of other secretory pathway glycosylation enzymes.

  大鼠内切糖苷酶是一种糖苷酶，可催化二糖、三糖或四糖（Glc1-3Man）从带有末端葡萄糖残基的 N-糖基化中间产物中裂解出来。迄今为止，它是这类内糖苷酶中唯一有特征的成员。虽然该蛋白已被证实定位在高尔基体腔膜上，但其发生机制尚未确定。利用大鼠内切甘露糖苷酶序列，我们确定了三个同源物，在人类、小鼠和大鼠基因组中各有一个。四个编码蛋白序列的比对结果表明，新发现的序列高度保守，但在 N 端与之前报道的蛋白有显著差异。在这项研究中，我们从大鼠和人类的 cDNA 文库中克隆了两个新的内切糖苷酶序列，但未能扩增出之前报道的大鼠序列的开放阅读框。对大鼠基因组的分析证实，之前报道的序列的 59 端和 39 端实际上位于不同的染色体上。这一点，再加上我们无法扩增之前报道的序列，表明之前发表的大鼠内切甘露糖苷酶序列的 N 端很可能是错误的（克隆假象），而本次研究中报道的序列编码的是完整的蛋白质。此外，与之前的序列不同，本研究中发现的三个 ORF 编码的蛋白含有一个 N 端跨膜结构域。在这里，我们证明了这一区域负责高尔基体的定位，从而证实了内切甘露糖苷酶与其他大多数分泌途径糖基化酶一样，是一种 II 型膜蛋白。
• Asparagine-linked glycoprotein biosynthesis in rat brain: Identification of glucosidase I, glucosidase II, and an endomannosidase (glucosyl mannosidase)
  作者：D.R.P. Tulsiani、Vera D. Coleman、Oscar Touster

  DOI：10.1016/0003-9861(90)90558-g

  日期：1990.2

  our conclusion that, as in other tissues, rat brain glucosidase I cleaves alpha 1,2-linked terminal glucosyl residues, whereas glucosidase II prefers alpha 1,3-linked glucosyl residues. In addition to these two processing glucosidases, we have characterized an endo enzyme (glucosyl mannosidase) in rat brain. The endomannosidase cleaves a disaccharide (glucosyl alpha 1,3-mannose) from monoglucosylated

  该实验室先前的研究提供了证据，主要是基于新的α-D-甘露糖苷酶的存在，表明与其他组织相比，脑中N-连接的糖蛋白的生物合成可能有所不同（Tulsiani，DRP和Touster，O （1985）J. Biol。Chem。260，13,081-13,087）。在本报告中，我们描述了对涉及早期加工反应的酶的研究。这些研究表明，大脑与其他组织一样，都含有糖苷酶I和II。通过在DE-52柱上的色谱分离两种葡糖苷酶作为不同的活性，并且有一些重叠。差异抑制研究和底物特异性研究支持我们的结论，即在其他组织中，大鼠脑中的葡糖苷酶I裂解α1,2连接的末端葡糖基残基，而葡糖苷酶II则首选α1，3-连接的葡糖基残基。除了这两种加工的葡糖苷酶，我们还对大鼠脑中的内切酶（葡糖基甘露糖苷酶）进行了表征。内切甘露糖苷酶从单糖基化的寡糖（GlcMan7-9GlcNAc）切割二糖（葡糖基α1,3-甘露糖）。当使用二或三葡萄糖
• Molecular Cloning and Expression of Rat Liver Endo-α-mannosidase, an N-Linked Oligosaccharide Processing Enzyme
  作者：Mary Jane Spiro、Vishnu D. Bhoyroo、Robert G. Spiro

  DOI：10.1074/jbc.272.46.29356

  日期：1997.11

  A clone containing the open reading frame of endo-alpha-D-mannosidase, an enzyme involved in early N-linked oligosaccharide processing, has been isolated from a rat liver lambdagt11 cDNA library. This was accomplished by a strategy that involved purification of the endomannosidase from rat liver Golgi by ligand affinity chromatography (Hiraizumi, S., Spohr, U., and Spiro, R. G. (1994) J. Biol. Chem

  从大鼠肝lambdagt11 cDNA文库中分离出一个克隆，该克隆含有一个内切α-D-甘露糖苷酶的开放阅读框，该酶参与早期的N-连接寡糖加工。这是通过涉及通过配体亲和层析从大鼠肝脏高尔基体中纯化内甘露糖苷酶的策略来实现的（Hiraizumi，S.，Spohr，U。和Spiro，RG（1994）J.Biol.Chem.269，4697-4700）。电泳和制备电泳，然后确定胰蛋白酶肽的序列。使用基于这些序列的简并引物，以大鼠肝脏cDNA为模板的聚合酶链式反应产生了一个470个碱基对的产物，适用于文库筛选和Northern blot杂交。纯化的λDNA的EcoRI消化释放了一个5.4 kb的片段，该片段在Bluescript II SK（-）载体中得到了扩增。序列分析表明，推导的内切甘露糖苷酶的开放阅读框从核苷酸89延伸至1441，编码451个氨基酸的蛋白质，对应的分子量为52 kDa。数据库搜
• Synthesis of α-D-Glucopyranosyl-(1-3)-α-D-Mannopyranosyl-(1-7)-4-Methylumbelliferone, A Fluorogenic Substrate for Endo-α-1,2-Mannosidase
  作者：C. Vogel、G. Pohlentz

  DOI：10.1080/07328300008544148

  日期：2000.1.1

  alpha -D-Glucopyranosyl-(1-3)-alpha -D-mannopyranosyl-(1-7)-4-methylumbelliferone (Glc-Man-Muf) was synthesized as a potential fluorogenic substrate for endo-alpha -1,2-mannosidase. The synthesis was designed in a convergent way. The glucose donor ethyl 2,3,4,6-tetra-O-benzyl-1-thio-beta -glucopyranoside and the mannose acceptor 1,2:4,6-di-O-isopropylidene-beta -mannopyranose were coupled in the presence of N-iodosuccinimide and trifluoromethanesulfonic acid to yield the corresponding disaccharide derivative. After conversion into peracetylated alpha -D-glucopyranosyl-(1-3)-alpha -D-mannopyranose the disaccharide was attached to 4-methylumbelliferone using the Helferich method. After separation of the desired isomer, deacetylation yielded the title compound. Glc-Man-Muf was used as st substrate in endomannosidase assays with rat liver Golgi preparations as an enzyme source (in the presence of the alpha -glucosidase inhibitor deoxynojirimycin). The degradation of Glc-Man-Muf was linear with protein up to 300 mug and with time up to 2 h. V-max and K-m were determined to be 0.17 nmol/mg x h and 3.7 mM, respectively.