α-isomaltose | 35867-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-isomaltose
• 英文别名: D-(+)-Gentiobiose；α-D-glucopyranosyl-(1 → 6)-α-D-glucopyranose；α-D-glucopyranosyl-(1→6)-α-D-glucopyranose；α-D-Glcp-(1->6)-D-Glcp；Isomaltose；alpha-Isomaltose；(2S,3R,4S,5S,6R)-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxane-2,3,4,5-tetrol
• CAS: 35867-21-1
• 化学式: C₁₂H₂₂O₁₁
• 分子量: 342.3
• InChiKey: DLRVVLDZNNYCBX-NCFXGAEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.7
• 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-isomaltose 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：

  isomaltotriose 在 盐酸 作用下， 以 水 为溶剂， 反应 1.5h， 生成 D-葡萄糖 、 α-isomaltose
  参考文献：
  名称：

  Acetolysis of Leuconostoc mesenteroides NRRL B-1299 dextran. Isolation and characterization of oligosaccharides containing secondary linkages from the borate-soluble fraction

  摘要：

  Fractionation of the deacetylated acetolyzate of the borate-soluble fraction of the dextran elaborated by L. mesenteroides NRRL B-1299 gave, after chromatography on charcoal-Celite, preparative paper-chromatography, and paper electrophoresis, 4 trisaccharide fractions and 4-tetrasaccharide fractions. The isolated oligosaccharides were characterized by their paper-chromatographic mobility, examination of partial acid-hydrolyzates of the oligosaccharides and their corresponding alditols, and methylation analysis. These oligosaccharides were kojitriose, isomaltotriose, a mixture of 2-O-.alpha.-isomaltosyl-D-glucose, 21-O-.alpha.-D-glucosylisomaltose and 2-O-.alpha.-nigerosyl-D-glucose, 6-O-.alpha.-kojibiosyl-D-glucose, isomaltotetraose, a mixture of 2-O-.alpha.-isomaltotriosyl-D-glucose and 21-O-.alpha.-D-glucosylisomaltotriose, 6-O-.alpha.-kojitriosyl-D-glucose and 63-O-.alpha.-D-glucosylkojitriose, respectively. Some of these oligosaccharides are newly isolated and characterized.

  DOI：

  10.1016/s0008-6215(00)85371-9

文献信息

• Synthesis of peptides and oligosaccharides by using a recyclable fluorous tag
  作者：Kohtaro Goto、Tsuyoshi Miura、Mamoru Mizuno

  DOI：10.1016/j.tetlet.2005.09.160

  日期：2005.11

  A hexakis(fluorous chain)-type alcohol was used in the synthesis of oligosaccharides and peptides through connection with a linker suitable for the particular type of target compound. After the preparation of the desired compound, the fluorous alcohol was easily recovered in good yields under basic conditions. It appears that the fluorous alcohol can be recovered, recycled, and reused.

  通过与适合特定类型目标化合物的接头连接，六（氟链）型醇用于寡糖和多肽的合成。制备所需化合物后，在碱性条件下容易以高收率回收氟代醇。看来氟代醇可以回收，再循环和再利用。
• Modeling of enzymatic production of isomaltooligosaccharides: a mechanistic approach
  作者：Anindya Basu、Sarma Mutturi、Siddalingaiya Gurudutt Prapulla

  DOI：10.1039/c5cy00003c

  日期：——

  In the current investigation the production of isomaltooligosaccharides (IMO) by transglucosylation of maltose using α-glucosidase was modeled by a mechanistic approach. Parameters are estimated by a genetic algorithm followed by sensitivity analysis and experimental validation.

  在当前的调查中，通过机械方法对利用α-葡萄糖苷酶对麦芽糖进行转葡糖基化生产异麦芽低聚糖（IMO）进行了建模。参数通过遗传算法进行估计，然后进行敏感性分析和实验验证。
• Gluco-oligomers initially formed by the reuteransucrase enzyme of Lactobacillus reuteri 121 incubated with sucrose and malto-oligosaccharides
  作者：Justyna M Dobruchowska、Xiangfeng Meng、Hans Leemhuis、Gerrit J Gerwig、Lubbert Dijkhuizen、Johannis P Kamerling

  DOI：10.1093/glycob/cwt048

  日期：2013.9

  The probiotic bacterium Lactobacillus reuteri 121 produces a complex, branched (1 → 4, 1 → 6)-α-d-glucan as extracellular polysaccharide (reuteran) from sucrose (Suc), using a single glucansucrase/glucosyltransferase (GTFA) enzyme (reuteransucrase). To gain insight into the reaction/product specificity of the GTFA enzyme and the mechanism of reuteran formation, incubations with Suc and/or a series of malto-oligosaccharides (MOSs) (degree of polymerization (DP2–DP6)) were followed in time. The structures of the initially formed products, isolated via high-performance anion-exchange chromatography, were analyzed by matrix-assisted laser-desorption ionization time-of-flight mass spectrometry and 1D/2D 1H/13C NMR spectroscopy. Incubations with Suc only, acting as both donor and acceptor, resulted in elongation of Suc with glucose (Glc) units via alternating (α1 → 4) and (α1 → 6) linkages, yielding linear gluco-oligosaccharides up to at least DP ∼ 12. Simultaneously with the ensemble of oligosaccharides, polymeric material was formed early on, suggesting that alternan fragments longer than DP ∼ 12 have higher affinity with the GTFA enzyme and are quickly extended, yielding high-molecular-mass branched reuteran (4 × 107 Da). MOSs (DP2–DP6) in the absence of Suc turned out to be poor substrates. Incubations of GTFA with Suc plus MOSs as substrates resulted in preferential elongation of MOSs (acceptors) with Glc units from Suc (donor). This apparently reflects the higher affinity of GTFA for MOSs compared with Suc. In accordance with the GTFA specificity, most prominent products were oligosaccharides with an (α1 → 4)/(α1 → 6) alternating structure.

  益生菌吕特氏乳杆菌（Lactobacillus reuteri）121利用一种单一的葡聚糖琥珀酸酶/葡糖基转移酶（GTFA）（reuteransucrase），从蔗糖（Suc）中产生一种复杂的支链（1→4，1→6）-α-d-葡聚糖作为胞外多糖（reuteran）。为了深入了解 GTFA 酶的反应/产物特异性和芦丁聚糖的形成机制，对 Suc 和/或一系列麦芽寡糖（MOS）（聚合度为 DP2-DP6）的孵育过程进行了及时跟踪。最初形成的产物通过高效阴离子交换色谱法分离出来，并通过基质辅助激光解吸电离飞行时间质谱法和 1D/2D 1H/13C NMR 光谱法分析其结构。在同时作为供体和受体的 Suc 诱导下，Suc 通过交替 (α1 → 4) 和 (α1 → 6) 连接与葡萄糖（Glc）单元发生伸长，产生线性葡萄糖寡糖，至少达到 DP ∼ 12。在低聚糖集合的同时，很早就形成了聚合物质，这表明长于 DP ∼ 12 的交替聚糖片段与 GTFA 酶的亲和力较高，并能迅速延伸，产生高分子质量的支链芦丁聚糖（4 × 107 Da）。在没有 Suc 的情况下，MOSs（DP2-DP6）是较差的底物。将 GTFA 与作为底物的 Suc 和 MOS 一起培养，结果是 MOS（接受者）优先与来自 Suc（供体）的 Glc 单位发生延伸。这显然反映出与 Suc 相比，GTFA 对 MOS 的亲和力更高。根据 GTFA 的特异性，最主要的产物是具有（α1 → 4）/（α1 → 6）交替结构的寡糖。
• Enzymatic Synthesis and Structural Characterization of Theanderose through Transfructosylation Reaction Catalyzed by Levansucrase from <i>Bacillus subtilis</i> CECT 39
  作者：Laura Ruiz-Aceituno、Maria Luz Sanz、Blanca de las Rivas、Rosario Muñoz、Sofia Kolida、Maria Luisa Jimeno、F. Javier Moreno

  DOI：10.1021/acs.jafc.7b03092

  日期：2017.12.6

  was obtained after only 1 h and at a moderate temperature (37 °C), leading to high productivity (109.7–130.4 g L–1h–1) and yield (up to 37.3%) values. The enzymatic synthesis was highly regiospecific, since no other detectable acceptor reaction products were formed. The development of efficient and cost-effective procedures for the biosynthesis of unexplored but appealing oligosaccharides as potential

  这项工作解决了山梨糖的高产量和快速酶促生产的作用，山竹糖是一种天然存在的碳水化合物，也称为异麦芽蔗糖，其通过NMR测定的化学结构为α- d-吡喃葡萄糖基-（1→6）-α- d-吡喃葡萄糖基-（ 1→2）-β- d-果糖呋喃糖。通过使用四种不同的蔗糖：异麦芽糖浓度比，描述了异麦芽糖在枯草芽孢杆菌CECT 39蔗糖酶催化的反式果糖基化反应中充当受体的能力，可在存在蔗糖作为供体的情况下有效产生山竹糖。最大山竹糖浓度范围为122.4至130.4 g L –1在中等温度（37°C）下仅1 h即可获得，从而提高了生产率（109.7–130.4 g L –1 h –1）和产率（最高37.3％）。酶促合成具有高度区域特异性，因为没有形成其他可检测的受体反应产物。为未开发但吸引人的寡糖作为潜在的甜味剂（如山竹糖）进行生物合成的有效和具有成本效益的程序的开发，可能有助于扩大其潜在的应用范围，而该应用目前受到其低可用性的限制。
• Discovery of a novel glucanohydrolase, 4-α-isomaltooligosylglucose 4-glucanohydrolase, that can be used for efficient production of isomaltose
  作者：Noriaki Kitagawa、Hikaru Watanabe、Tetsuya Mori、Hajime Aga、Shimpei Ushio、Koryu Yamamoto

  DOI：10.1016/j.carres.2022.108578

  日期：2022.7

  We discovered a novel enzyme in our pursuit of an improved method for the production of isomaltose. The enzyme, 4-α-isomaltooligosylglucose 4-glucanohydrolase from Sarocladium kiliense U4520, recognizes the panose motif (α-d-Glcp-(1 → 6)-α-d-Glcp-(1 → 4)-d-Glcp) and hydrolyzes the α-1,4-glucosidic bond on the reducing end side with respect to the α-1,6-glucosidic bond. The structure on the non-reducing

  我们在寻求改进异麦芽糖生产方法的过程中发现了一种新型酶。来自Sarocladium kiliense U4520的 4-α-异麦芽寡糖基葡萄糖 4-葡聚糖水解酶可识别泛糖基序 (α- d -Glc p -(1 → 6)-α- d -Glc p -(1 → 4)- d -Glc p )，水解α-1,6-糖苷键的还原端侧的α-1,4-糖苷键。panose 基序非还原端的结构对于酶识别底物很重要，并且底物特异性是独特的，与以前报道的酶不同。该酶催化panose的水解，具有kcat /K m为31.2 s -1 mM -1，催化作用导致异头倒转。这些酶促特性表明，该酶可与球孢芽孢杆菌N75 中的 1,4-α-葡聚糖 6-α-葡糖基转移酶很好地配对，从而有效地从淀粉中生产异麦芽糖。