4-α-isomaltotriosylglucose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-α-isomaltotriosylglucose
• 英文别名: Glc(a1-6)Glc(a1-6)Glc(a1-4)a-Glc；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3S,4R,5R,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxan-2-yl]methoxy]oxan-2-yl]methoxy]oxane-3,4,5-triol
• 化学式: C₂₄H₄₂O₂₁
• 分子量: 666.585
• InChiKey: ATSPLDSNUFFQBC-TZFJCFQPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  45
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  348
• 氢给体数：
  14
• 氢受体数：
  21

反应信息

• 作为反应物：
  描述：

  4-α-isomaltotriosylglucose 在 4-α-isomaltooligosylglucose 4-glucanohydrolase from Sarocladium kiliense U4520 作用下， 以 aq. phosphate buffer 为溶剂， 反应 0.33h， 生成 a-无水葡萄糖酯 、 O-α-D-glucopyranosyl-(1<*>6)-O-α-D-glucopyranosyl-(1<*>6)-O-α-D-glucopyranose
  参考文献：
  名称：

  发现一种新型葡聚糖水解酶 4-α-异麦芽寡糖基葡萄糖 4-葡聚糖水解酶，可用于高效生产异麦芽糖

  摘要：

  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。

  DOI：

  10.1016/j.carres.2022.108578
• 作为产物：
  描述：

  蔗糖 、 D-(+)-纤维二糖 在 alternansucrase ASR C-del bis sodium acetate 作用下， 以 水 为溶剂， 以28%的产率得到panose
  参考文献：
  名称：

  Fully active alternansucrases partially deleted in its carboxy-terminal and amino-terminal domains and mutants thereof

  摘要：

  提供了截断或突变的交替糖基转移酶的核酸序列，包含这些核酸序列的载体，以及转化了编码截断或突变的交替糖基转移酶的核酸序列的宿主细胞。此外，还描述了一种重组交替糖基转移酶的过程，该过程具有高水平的表达，并保留酶活性。

  公开号：

  US20060127328A1

文献信息

• 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。
• Structural characterization of the maltose acceptor-products synthesized by Leuconostoc mesenteroides NRRL B-1299 dextransucrase
  作者：Marguerite Dols、Magali Remaud Simeon、René-Marc Willemot、Michel R. Vignon、Pierre F. Monsan

  DOI：10.1016/s0008-6215(97)10063-5

  日期：1997.12

  The glucooligosaccharides (GOS), produced by Leuconostoc mesenteroides NRRL B-1299 dextransucrase through an acceptor reaction with maltose and sucrose, were purified by reverse phase chromatography. Logarithmic plots of retention time vs. dp of the GOS gave three parallel lines suggesting the existence of at least three families of homologous molecules. The structure (C-13 and H-1 NMR spectroscopy) and reactivity of the purified molecules of the three families were investigated. All the products bear a maltose residue at the reducing end. The GOS in the first family (named OD) contained additional glucosyl residues all alpha-(1-->6) linked. The smallest molecule in this first series was panose or alpha-D-glucopyranosyl-(1-->6)-D-maltose (dp 3). All the OD molecules were shown to be good accepters for dextransucrase in the presence of sucrose. The second family, named R, was composed of linear GOS containing alpha-(1-->6)-linked glucosyl residues and a terminal alpha-(1-->2)-linked residue at the non-reducing end of the molecule; the smallest molecule in this family was alpha-D-glucopyranosyl-(1-->2)-D-panose (dp 4). The third family, R', was formed of GOS containing additional residues linked through alpha-(1-->6) linkages that constitute the linear chain, and an alpha-(1-->2)-branched residue located on the penultimate element of the chain, near the non-reducing end. The smallest molecule in this series is alpha-D-glucopyranosyl-(1-->6)-[alpha-D-glucopyranosyl-(1-->2)]-alpha-D-glucopyranosyl-(1-->6)-D-panose, dp 6, R and R' GOS are very poor accepters for L. mesenteroides NRRL B-1299 dextransucrase. This study makes it possible to suggest a rather simple reaction scheme, where molecules R-i, R'(i) and ODi of the same dp all result from the glucosylation of the same GOS: ODi-l (C) 1998 Elsevier Science Ltd.
• Fully active alternansucrases partially deleted in its carboxy-terminal and amino-terminal domains and mutants thereof
  申请人：Monsan Pierre

  公开号：US20060127328A1

  公开（公告）日：2006-06-15

  Nucleic acid sequences of truncated or mutated alternansucrases, vectors containing these nucleic acids sequences, host cells transformed with the nucleic acid sequences encoding truncated or mutated alternansucrases are provided. Furthermore, a process to recombinantly alternansucrase with a high level of expression, while retaining the enzymatic activity is described.

  提供了截断或突变的交替糖基转移酶的核酸序列，包含这些核酸序列的载体，以及转化了编码截断或突变的交替糖基转移酶的核酸序列的宿主细胞。此外，还描述了一种重组交替糖基转移酶的过程，该过程具有高水平的表达，并保留酶活性。
• 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。