α-nigerose | 52485-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-nigerose
• 英文别名: nigerose；3-O-alpha-d-glucopyranosyl-alpha-d-glucopyranose；(2S,3R,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
• CAS: 52485-08-2
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: QIGJYVCQYDKYDW-NMCXEIBESA-N

物化性质

• 沸点：
  690.5±55.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  α-nigerose 在 Streptococcus mutans dextran glucosidase 、 bovine serum albumin 作用下， 以 aq. acetate buffer 为溶剂， 反应 0.17h， 生成 a-无水葡萄糖酯
  参考文献：
  名称：

  Structural elements responsible for the glucosidic linkage‐selectivity of a glycoside hydrolase family 13 exo‐glucosidase

  摘要：

  Glycoside hydrolase family 13 contains exo‐glucosidases specific for α‐(1 → 4)‐ and α‐(1 → 6)‐linkages including α‐glucosidase, oligo‐1,6‐glucosidase, and dextran glucosidase. The α‐(1 → 6)‐linkage selectivity of Streptococcus mutans dextran glucosidase was altered to α‐(1 → 4)‐linkage selectivity through site‐directed mutations at Val195, Lys275, and Glu371. V195A showed 1300‐fold higher k cat/K m for maltose than wild‐type, but its k cat/K m for isomaltose remained 2‐fold higher than for maltose. K275A and E371A combined with V195A mutation only decreased isomaltase activity. V195A/K275A, V195A/E371A, and V195A/K275A/E371A showed 27‐, 26‐, and 73‐fold higher k cat/K m for maltose than for isomaltose, respectively. Consequently, the three residues are structural elements for recognition of the α‐(1 → 6)‐glucosidic linkage.

  DOI：

  10.1016/j.febslet.2015.02.023
• 作为产物：
  描述：

  Phenyl-carbamic acid (2R,3R,4S,5R,6R)-4-allyloxy-3,5-bis-benzyloxy-6-{2-[4-(toluene-4-sulfonylamino)-phenyl]-ethoxy}-tetrahydro-pyran-2-ylmethyl ester 在 Wilkinson's catalyst 、 氨 、 sodium 、 mercury dichloride 、 mercury(II) oxide 作用下， 以 乙醚 为溶剂， 反应 0.5h， 生成 α-nigerose
  参考文献：
  名称：

  α-和β-（1→2）-和-（1→3）连接的吡喃葡萄糖二糖及其蛋白结合物的合成

  摘要：

  摘要2,3,4-三-O-苄基-6-O-（N-苯基氨基甲酰基）-1-O-甲苯磺酰基-d-吡喃葡萄糖和3,4,6-三-O-苄基-2-O-p使-硝基苯甲酰基-1-O-甲苯磺酰基-d-吡喃葡萄糖与部分封闭的2- [4-（对甲苯磺酰胺基）苯基]乙基α-和β-d-吡喃葡萄糖苷反应。结构为α-d -Glc p-（1→2）-α-d -Glc p的二糖，α-d -Glc p-（1→3）-α-d -Glc p，β-d -Glc p合成了-（1→2）-β-d-Glcp和β-d-Glcp-（1→3）-α-d-Glcp。将寡糖在液体氨中用钠脱苄基，得到具有游离伯芳族氨基的二糖，将其转化为异硫氰酸酯衍生物，然后与各种蛋白质偶联，得到相应的缀合物。

  DOI：

  10.1016/s0008-6215(00)88056-8

文献信息

• Acceptor reactions of alternansucrase from Leuconostoc mesenteroides NRRL B-1355
  作者：Gregory L. Côté、John F. Fobyt

  DOI：10.1016/0008-6215(82)85013-1

  日期：1982.12

  Extracellular glucansucrases from various bacterial sources, including Leuconostoc mesenteroides, have been shown to catalyze the transfer of glucosyl groups from sucrose to low-molecular-weight acceptor sugars, forming a series of oligosaccharides. An extracellular glucansucrase recently isolated from Leuconostoc mesenteroides NRRL B-1355 synthesizes a polysaccharide consisting of alternating α-(1→6)-

  来自各种细菌来源的细胞外葡聚糖蔗糖，包括肠间叶亮葡菌，已显示出可将葡萄糖基团从蔗糖转移至低分子量受体糖，从而形成一系列寡糖。最近从肠膜肠球菌NRNR B-1355中分离出的一种细胞外葡糖苷酶合成了由交替的α-（1→6）-和α-（1→3）连接的d-葡萄糖残基组成的多糖。我们已经发现，在许多低分子量受体糖存在下，这种酶制剂能够形成α-（1→6）-和α-（1→3）-连接的受体产物。d-葡萄糖仅产生异麦芽糖，没有形成黑糖。相似地，甲基α-d-葡萄糖苷，甲基β-d-葡萄糖苷，麦芽糖和黑糖生成了甲基α-异麦芽糖苷，甲基β-异麦芽糖苷，panose和62-O-α-d-葡萄糖基黑麦芽糖，分别。然而，异麦芽糖同时给出了异麦芽三糖和32-O-α-d-葡萄糖基异麦芽糖。这些初始的受体产物也可以充当受体，并且较高dp产物的结构表明，只有当非还原性葡萄糖受体基团通过α-连接时，才形成（1→3）-α-d-糖苷键。 （
• Rational design of an improved transglucosylase for production of the rare sugar nigerose
  作者：Jorick Franceus、Shari Dhaene、Hannes Decadt、Judith Vandepitte、Jurgen Caroen、Johan Van der Eycken、Koen Beerens、Tom Desmet

  DOI：10.1039/c9cc01587f

  日期：——

  The sucrose phosphorylase from Bifidobacterium adolescentis (BaSP) can be used as a transglucosylase for the production of rare sugars. We designed variants of BaSP for the efficient synthesis of nigerose from sucrose and glucose, thereby adding to the inventory of rare sugars that can conveniently be produced from bulk sugars.

  来自青春双歧杆菌（BaSP）的蔗糖磷酸化酶可用作生产稀有糖的转葡糖基化酶。我们设计了BaSP的变体，用于从蔗糖和葡萄糖中高效合成黑糖，从而增加了可从散装糖中方便地生产的稀有糖的库存。
• 1H-NMR-Untersuchungen zur Spaltspezifität von α- und β-d-Glucosidasen gegenäber Disacchariden. II
  作者：Rudi Wajda、Mario König、Horst Ludwig、Sigrid Mronga、Horst Friebolin

  DOI：10.1016/0008-6215(92)80094-h

  日期：1992.11

  hydrolysis of six disaccharides having D-glucose units, i.e., cellobiose, laminarabiose, gentiobiose, maltose, nigerose, and isomaltose. β- d -Glucosidase from sweet almonds was used to hydrolyze the three β- d -glucosidic-linked disaccharides, and the three α- d -glucosidic-linked disaccharides were hydrolyzed by maltase from bakers yeast. The results showed that the rate of hydrolysis depends strongly on

  摘要1H NMR光谱法用于测定六种具有D-葡萄糖单元的二糖的酶促水解速率，所述二糖为纤维二糖，拉米纳糖，龙胆二糖，麦芽糖，黑糖和异麦芽糖。用甜杏仁中的β-d-葡糖苷酶水解三种β-d-葡糖苷键联的二糖，并将三种α-d-葡糖苷键合二糖用面包酵母中的麦芽糖酶水解。结果表明，水解速率在很大程度上取决于OH-1的位置。动力学研究直接得出了在低底物浓度下两种端基异构体酶促水解的一级速度常数的商（底物浓
• Structural elements responsible for the glucosidic linkage‐selectivity of a glycoside hydrolase family 13 exo‐glucosidase
  作者：Wataru Saburi、Hiroaki Rachi-Otsuka、Hironori Hondoh、Masayuki Okuyama、Haruhide Mori、Atsuo Kimura

  DOI：10.1016/j.febslet.2015.02.023

  日期：2015.3.24

  Glycoside hydrolase family 13 contains exo‐glucosidases specific for α‐(1 → 4)‐ and α‐(1 → 6)‐linkages including α‐glucosidase, oligo‐1,6‐glucosidase, and dextran glucosidase. The α‐(1 → 6)‐linkage selectivity of Streptococcus mutans dextran glucosidase was altered to α‐(1 → 4)‐linkage selectivity through site‐directed mutations at Val195, Lys275, and Glu371. V195A showed 1300‐fold higher k cat/K m for maltose than wild‐type, but its k cat/K m for isomaltose remained 2‐fold higher than for maltose. K275A and E371A combined with V195A mutation only decreased isomaltase activity. V195A/K275A, V195A/E371A, and V195A/K275A/E371A showed 27‐, 26‐, and 73‐fold higher k cat/K m for maltose than for isomaltose, respectively. Consequently, the three residues are structural elements for recognition of the α‐(1 → 6)‐glucosidic linkage.
• The synthesis of α- and β-(1 → 2)- and -(1 → 3)-linked glucopyranose disaccharides and their protein conjugates
  作者：Ronald Eby、Conrad Schuerch

  DOI：10.1016/s0008-6215(00)88056-8

  日期：1982.4

  -toluenesulfonamido)phenyl]ethyl α- and β- d -glucopyranosides. Disaccharides having the structure α- d -Glc p -(1 → 2)-α- d -Glc p , α- d -Glc p -(1 → 3)-α- d -Glc p , β- d -Glc p -(1 → 2)-β- d -Glc p , and β- d -Glc p -(1 → 3)-α- d -Glc p were synthesized. The oligosaccharides were debenzylated with sodium in liquid ammonia to give disaccharides having a free primary aromatic amino group, which were converted

  摘要2,3,4-三-O-苄基-6-O-（N-苯基氨基甲酰基）-1-O-甲苯磺酰基-d-吡喃葡萄糖和3,4,6-三-O-苄基-2-O-p使-硝基苯甲酰基-1-O-甲苯磺酰基-d-吡喃葡萄糖与部分封闭的2- [4-（对甲苯磺酰胺基）苯基]乙基α-和β-d-吡喃葡萄糖苷反应。结构为α-d -Glc p-（1→2）-α-d -Glc p的二糖，α-d -Glc p-（1→3）-α-d -Glc p，β-d -Glc p合成了-（1→2）-β-d-Glcp和β-d-Glcp-（1→3）-α-d-Glcp。将寡糖在液体氨中用钠脱苄基，得到具有游离伯芳族氨基的二糖，将其转化为异硫氰酸酯衍生物，然后与各种蛋白质偶联，得到相应的缀合物。