manninotriose | 499-39-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: manninotriose
• 英文别名: α-D-galactopyranosyl-(1→6)-α-D-galactopyranosyl-(1→6)-D-glucopyranose；D-Gal alpha 1->6D-Gal alpha 1->6D-Glucose；(3R,4S,5S,6R)-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• CAS: 499-39-8
• 化学式: C₁₈H₃₂O₁₆
• 分子量: 504.442
• InChiKey: FBJQEBRMDXPWNX-SMGIPPFUSA-N

物化性质

• 沸点：
  952.8±65.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.9
• 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

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  蜜二糖	D-melibiose	5340-95-4	C12H22O11	342.3
  麦芽糖	Maltose	16984-36-4	C12H22O11	342.3
  ——	Lactose	63-42-3	C12H22O11	342.3
  D-水苏糖	stachyose	470-55-3	C24H42O21	666.585
  蔗糖	Sucrose	57-50-1	C12H22O11	342.3

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	O-α-D-galactopyranosyl-(1->6)-O-α-D-galactopyranosyl-(1->6)-O-D-glutitol	937251-96-2	C18H34O16	506.458

反应信息

• 作为反应物：
  描述：

  manninotriose 在 sodium tetrahydroborate 作用下， 以 水 为溶剂， 反应 0.17h， 以71%的产率得到O-α-D-galactopyranosyl-(1->6)-O-α-D-galactopyranosyl-(1->6)-O-D-glutitol
  参考文献：
  名称：

  从Stachys sieboldi Miq合成新的糖衍生物，并对结核分枝杆菌，鸟分枝杆菌和金黄色葡萄球菌进行抗菌评估。

  摘要：

  从水苏糖中提取了一系列的糖衍生物（7-14），水苏糖为水苏木的糖化合物，并评估了其对结核分枝杆菌，鸟分枝杆菌和金黄色葡萄球菌的抗菌活性，并研究了它们的结构-活性关系。结果显示化合物OCT359（烯丙基O-（2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基）-（1-> 6）-O-（2,3,4-三-O-乙酰基-α-D-吡喃半乳糖基）-（1-> 6）-O-2,3,4-三-O-乙酰基-β-D-吡喃葡萄糖苷）（12）表现出体外抗菌活性。C-1处的烯丙基和甘露糖苷的乙酰氧基是抗菌活性所必需的。

  DOI：

  10.1016/j.bmcl.2007.02.024
• 作为产物：
  描述：

  4-硝基苯基-α-D-吡喃半乳糖苷 在 recombinant Aspergillus nidulans FGSC GH36 α-galactosidase 作用下， 反应 6.0h， 生成 manninotriose
  参考文献：
  名称：

  糖苷水解酶家族36的构巢曲霉α-半乳糖苷酶通过转糖基化催化α-半乳糖低聚糖的形成

  摘要：

  来自构巢曲霉（AglC）的α-半乳糖苷酶属于系统发育簇，包含糖苷水解酶家族36（GH36）的真核α-半乳糖苷酶和α-半乳糖寡糖合酶。重组AglC在大肠杆菌中以His-tag融合形式高产量（0.65 g·L -1培养）产生，催化40 m m 4-硝基苯酚α- d-吡喃半乳糖苷具有α-（1→6）区域选择性的高效转糖基化作用，蜜二糖棉子糖或，产生4-硝基苯酚α-收率的37-74％d -Gal p - （1→6） - d -Gal p，α- d -Gal p - （1→6）-α- d-Gal p - （1→6） - d -Glc p和α- d -Gal p - （1→6）-α- d -Gal p - （1→6） - d -Glc p - （α1→β2 ）-d- Fru f（水苏糖）。此外，在10个候选单糖受体（400 m m）和供体4-硝基苯酚α- d-吡喃半乳糖苷（40 m m）中，还获得了由半

  DOI：

  10.1111/j.1742-4658.2010.07763.x

文献信息

• Transgalactosylation Catalyzed by<i>α</i>-Galactosidase from<i>Candida guilliermondii</i>H-404
  作者：Hiroyuki Hashimoto、Chie Katayama、Masaru Goto、Tatsuyuki Okinaga、Sumio Kitahata

  DOI：10.1271/bbb.59.619

  日期：1995.1

  The thermostable α-galactosidase from Candida guilliermondii H-404 synthesized self-transfer products in the absence of a suitable acceptor. The main self-transfer product, using melibiose as a donor substrate, was O-α-D-galactosyl-(1,6)-O-α-D-galactosyl-(1,6)-D-glucose. This enzyme had a wide acceptor specificity. D-Glucose, D-galactose, maltose, maltitol, and 1,4-butandiol were the most effective acceptors in the transgalactosylation catalyzed by this enzyme. The enzyme could also transfer α-galactosyl residues to pentoses (L-arabinose, D-xylose, and D-ribose) and methyl pentoses (D-fucose and L-rhamnose). The main transfer products to lactose, maltose, and sucrose as acceptors were identified as O-α-D-galactosyl-(1,6)-O-β-D-galactosyl-(1,4)-D-glucose, O-α-D-galactosyl-(1,6)-O-α-D-glucosyl-(1,4)-D-glucose, and O-α-D-galactosyl-(1,6)-O-α-D-glucosyl-(1,2)-β-D-fructoside (raffinose), respectively.

  来自Candida guilliermondii H-404的热稳定α-半乳糖苷酶在缺乏合适受体的情况下合成了自转移产物。主要自转移产物是以蜜二糖为供体底物的情况下，形成的O-α-D-半乳糖基-(1,6)-O-α-D-半乳糖基-(1,6)-D-葡萄糖。该酶具有广泛的受体特异性。在由该酶催化的转半乳糖作用中，D-葡萄糖、D-半乳糖、麦芽糖、麦芽糖醇和1,4-丁二醇是最有效的受体。该酶还能将α-半乳糖基转移至戊糖（L-阿拉伯糖、D-木糖和D-核糖）和甲基戊糖（D-岩藻糖和L-鼠李糖）。以乳糖、麦芽糖和蔗糖为受体时，主要转移产物分别被鉴定为O-α-D-半乳糖基-(1,6)-O-β-D-半乳糖基-(1,4)-D-葡萄糖、O-α-D-半乳糖基-(1,6)-O-α-D-葡萄糖基-(1,4)-D-葡萄糖和O-α-D-半乳糖基-(1,6)-O-α-D-葡萄糖基-(1,2)-β-D-果糖苷（棉子糖）。
• Isolation and structural elucidation of prebiotic oligosaccharides from Ziziphi Spinosae Semen
  作者：Juan Song、Yue Liu、Xiangchang Yin、Yi Nan、Yuhao Shi、Xiaojuan Chen、Haizhen Liang、Jie Zhang、Baiping Ma

  DOI：10.1016/j.carres.2023.108948

  日期：2023.12

  Six oligosaccharides were discovered and isolated for the first time from Ziziphi Spinosae Semen. On the basis of spectroscopic analysis, their structures were determined to be verbascose (1), verbascotetraose (2), stachyose (3), manninotriose (4), raffinose (5), and melibiose (6). The prebiotic effect of the oligosaccharide fraction was assayed by eight gut bacterial growth in vitro, revealing a significant

  首次从酸枣仁中发现并分离出六种低聚糖。根据光谱分析，确定其结构为毛蕊花糖( 1 )、毛蕊花四糖( 2 )、水苏糖( 3 )、甘露三糖( 4 )、棉子糖( 5 )和蜜二糖( 6 )。通过体外八种肠道细菌生长测定了寡糖组分的益生元作用，结果表明，嗜酸乳杆菌、加氏乳杆菌和约氏乳杆菌的细胞密度显着增加，高达 4 倍。评估了具有不同聚合度（DP）和结构的六种寡糖对嗜酸乳杆菌生长的影响。因此，与其他低聚糖相比，水苏糖和棉子糖对细菌生长具有卓越的支持作用。本研究探讨了棉子糖家族寡糖（RFO）的构效关系，结果表明，当寡糖具有相同分子量时，单糖类型越多，越有利于肠道细菌的生长。
• Study of Influential Factors on Oligosaccharide Formation by Fructosyltransferase Activity during Stachyose Hydrolysis by Pectinex Ultra SP-L
  作者：Antonia Montilla、Agustín Olano、Cristina Martínez-Villaluenga、Nieves Corzo

  DOI：10.1021/jf202472p

  日期：2011.10.12

  The influence of reaction conditions for oligosaccharide synthesis from stachyose using a commercial enzymatic preparation from Aspergillus aculeatus (Pectinex Ultra SP-L) was studied. Oligosaccharides were analyzed by gas chromatography with flame ionization detection (GC-FID) and matrix-assisted laser desorption/ionization-time-of-flight-mass spectrometry (MALDI-TOF-MS). Galactosyl-melibiose (DP3) was synthesized as a result of fructosidase activity, whereas fructosyl-stachyose (DP5) and difructosyl-stachyose (DP6) were formed as a consequence of the fructosyltransferase activity of Pectinex Ultra SP-L. The optimal reaction conditions for the synthesis of penta- and hexasaccharides were 60 degrees C, pH 5.5, 600 mg/mL stachyose, and 34 U/mL enzyme. Reaction time played an important role in oligosaccharide mixture composition constituted by 20% DP5, 0.7% DP6, 55% stachyose, 21% galactosyl-melibiose, and 1% monosaccharides after 1 h and 16% DP5, 4% DP6, 27% stachyose, 44% galactosyl-melibiose, and 2% monosaccharides after 3 h. In conclusion, stachyose could be used as a substrate for the enzymatic synthesis of new oligosaccharides that may open new opportunities in the development of future prebiotics.
• Aspergillus nidulansα-galactosidase of glycoside hydrolase family 36 catalyses the formation of α-galacto-oligosaccharides by transglycosylation
  作者：Hiroyuki Nakai、Martin J. Baumann、Bent O. Petersen、Yvonne Westphal、Maher Abou Hachem、Adiphol Dilokpimol、Jens Ø. Duus、Henk A. Schols、Birte Svensson

  DOI：10.1111/j.1742-4658.2010.07763.x

  日期：2010.9

  α‐galactosidase from Aspergillus nidulans (AglC) belongs to a phylogenetic cluster containing eukaryotic α‐galactosidases and α‐galacto‐oligosaccharide synthases of glycoside hydrolase family 36 (GH36). The recombinant AglC, produced in high yield (0.65 g·L−1 culture) as His‐tag fusion in Escherichia coli, catalysed efficient transglycosylation with α‐(1→6) regioselectivity from 40 mm 4‐nitrophenol α

  来自构巢曲霉（AglC）的α-半乳糖苷酶属于系统发育簇，包含糖苷水解酶家族36（GH36）的真核α-半乳糖苷酶和α-半乳糖寡糖合酶。重组AglC在大肠杆菌中以His-tag融合形式高产量（0.65 g·L -1培养）产生，催化40 m m 4-硝基苯酚α- d-吡喃半乳糖苷具有α-（1→6）区域选择性的高效转糖基化作用，蜜二糖棉子糖或，产生4-硝基苯酚α-收率的37-74％d -Gal p - （1→6） - d -Gal p，α- d -Gal p - （1→6）-α- d-Gal p - （1→6） - d -Glc p和α- d -Gal p - （1→6）-α- d -Gal p - （1→6） - d -Glc p - （α1→β2 ）-d- Fru f（水苏糖）。此外，在10个候选单糖受体（400 m m）和供体4-硝基苯酚α- d-吡喃半乳糖苷（40 m m）中，还获得了由半
• Synthesis of new sugar derivatives from Stachys sieboldi Miq and antibacterial evaluation against Mycobacterium tuberculosis, Mycobacterium avium, and Staphylococcus aureus
  作者：Taku Chiba、Takemasa Takii、Kenji Nishimura、Yoshifumi Yamamoto、Hiroko Morikawa、Chiyoji Abe、Kikuo Onozaki

  DOI：10.1016/j.bmcl.2007.02.024

  日期：2007.5

  A series of sugar derivatives (7-14) were synthesized from stachyose, a sugar compound of Stachys sieboldi Miq, and evaluated for antibacterial activity against Mycobacterium tuberculosis, Mycobacterium avium, and Staphylococcus aureus, and their structure-activity relationships were studied. The results showed that the compound OCT359 (allyl O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-(1-->6)-O-(2

  从水苏糖中提取了一系列的糖衍生物（7-14），水苏糖为水苏木的糖化合物，并评估了其对结核分枝杆菌，鸟分枝杆菌和金黄色葡萄球菌的抗菌活性，并研究了它们的结构-活性关系。结果显示化合物OCT359（烯丙基O-（2,3,4,6-四-O-乙酰基-α-D-吡喃半乳糖基）-（1-> 6）-O-（2,3,4-三-O-乙酰基-α-D-吡喃半乳糖基）-（1-> 6）-O-2,3,4-三-O-乙酰基-β-D-吡喃葡萄糖苷）（12）表现出体外抗菌活性。C-1处的烯丙基和甘露糖苷的乙酰氧基是抗菌活性所必需的。