1L-1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol | 75802-23-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1L-1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol
• 英文别名: O-(α-D-glucosaminepyranosyl)-(1→1)-D-myo-inositol；D-myo-inosityl 2-amino-2-deoxy-α-D-glucopyranoside；1-O-glucosamine-D-myo-inositol；X-14847
• CAS: 75802-23-2
• 化学式: C₁₂H₂₃NO₁₀
• 分子量: 341.315
• InChiKey: HEPUIGACZYVUCD-LFIKJOHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.04
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  206.32
• 氢给体数：
  9.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 1L-1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol 以 吡啶 为溶剂， 反应 18.0h， 生成 2-(Acetylamino)-2-deoxy-α-D-glucopyranosyl-1-O-D-myo-inositol Octaacetate
  参考文献：
  名称：

  Microbial products. 5. Absolute configuration of aminoglycoside X-14847

  摘要：

  DOI：

  10.1021/jo00315a029
• 作为产物：
  描述：

  Inositol 在 palladium on activated carbon 、 氢气 、 sodium methylate 、 二正丁基氧化锡 、 potassium carbonate 、 对甲苯磺酸 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 异丙醇 、 甲苯 为溶剂， -20.0~100.0 ℃ 、275.8 kPa 条件下， 反应 31.5h， 生成 1L-1-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol
  参考文献：
  名称：

  底物类似物的合成作为结核分枝杆菌MshC的潜在抑制剂

  摘要：

  麦考硫醇半胱氨酸连接酶（MshC）是麦考硫醇（MSH）生物合成中的关键酶，也是开发新型抗分枝杆菌化合物的有希望的目标。在本文中，我们报道了作为MshC酶潜在抑制剂的底物类似物的合成。使用施密特糖基化策略，使用对映体纯的肌醇受体和2-脱氧三氯乙酰亚氨酸酯糖基供体，以糖基化收率大于70％且总收率＞ 5％来合成靶分子。肌醇受体是通过（±）-肌醇的手性拆分而获得的。

  DOI：

  10.1016/j.carres.2017.10.014

文献信息

• Metabolic coupling of two small-molecule thiols programs the biosynthesis of lincomycin A
  作者：Qunfei Zhao、Min Wang、Dongxiao Xu、Qinglin Zhang、Wen Liu

  DOI：10.1038/nature14137

  日期：2015.2

  Mycothiol and ergothioneine are shown to have important roles in the biosynthesis of lincomycin A, a sulfur-containing antibiotic that is used to treat severe Gram-positive bacterial infections in people who cannot receive penicillin antibiotics. The biosynthetic origins of sulfur atoms found in natural products — or secondary metabolites — are not well understood. Mycothiol (MSH) is a cysteinyl pseudo-disaccharide found in Gram-positive actinobacteria, and the conjugation of this thiol-containing compound to electrophilic toxins facilitates their excretion from the bacterial cell. Actinomycetes also produce another thiol, ergothioneine (EGT), a histidine betaine derivative of unknown function. In this paper, the authors showed that MSH and EGT have important roles in the biosynthesis of lincomycin A, a sulfur-containing antibiotic that is used to treat severe Gram-positive bacterial infections in people who cannot receive penicillin antibiotics. Low-molecular-mass thiols in organisms are well known for their redox-relevant role in protection against various endogenous and exogenous stresses1,2,3. In eukaryotes and Gram-negative bacteria, the primary thiol is glutathione (GSH), a cysteinyl-containing tripeptide. In contrast, mycothiol (MSH), a cysteinyl pseudo-disaccharide, is dominant in Gram-positive actinobacteria, including antibiotic-producing actinomycetes and pathogenic mycobacteria. MSH is equivalent to GSH, either as a cofactor or as a substrate, in numerous biochemical processes4, most of which have not been characterized, largely due to the dearth of information concerning MSH-dependent proteins. Actinomycetes are able to produce another thiol, ergothioneine (EGT), a histidine betaine derivative that is widely assimilated by plants and animals for variable physiological activities5. The involvement of EGT in enzymatic reactions, however, lacks any precedent. Here we report that the unprecedented coupling of two bacterial thiols, MSH and EGT, has a constructive role in the biosynthesis of lincomycin A, a sulfur-containing lincosamide (C8 sugar) antibiotic that has been widely used for half a century to treat Gram-positive bacterial infections6,7,8,9. EGT acts as a carrier to template the molecular assembly, and MSH is the sulfur donor for lincomycin maturation after thiol exchange. These thiols function through two unusual S-glycosylations that program lincosamide transfer, activation and modification, providing the first paradigm for EGT-associated biochemical processes and for the poorly understood MSH-dependent biotransformations, a newly described model that is potentially common in the incorporation of sulfur, an element essential for life and ubiquitous in living systems.

  生物合成中的硫原子来源——或称次生代谢物——尚未得到充分理解。Mycothiol (MSH)是一种半胱氨酸类假二糖，存在于革兰氏阳性放线菌中，这种含硫化合物与亲电性毒素的结合有助于它们从细菌细胞中排出。放线菌还产生另一种硫醇——麦角硫因（ergothioneine，EGT），这是一种组氨酸甜菜碱衍生物，功能尚不清楚。在这篇论文中，作者指出，MSH和EGT在生物合成中的硫原子来源——或称次生代谢物——尚未得到充分理解。Mycothiol (MSH)是一种半胱氨酸类假二糖，存在于革兰氏阳性放线菌中，这种含硫化合物与亲电性毒素的结合有助于它们从细菌细胞中排出。放线菌还产生另一种硫醇——麦角硫因（ergothioneine，EGT），这是一种组氨酸甜菜碱衍生物，功能尚不清楚。在这篇论文中，作者指出，MSH和EGT在生物合成中的硫原子来源——或称次生代谢物——尚未得到充分理解。Mycothiol (MSH)是一种半胱氨酸类假二糖，存在于革兰氏阳性放线菌中，这种含硫化合物与亲电性毒素的结合有助于它们从细菌细胞中排出。放线菌还产生另一种硫醇——麦
• Synthesis of mycothiol, 1D-1-O-(2-[N-acetyl-l-cysteinyl]amino-2-deoxy-α-d-glucopyranosyl)-myo-inositol, principal low molecular mass thiol in the actinomycetes
  作者：M.Anwar Jardine、Hendrik S.C Spies、Comfort M Nkambule、David W Gammon、Daniel J Steenkamp

  DOI：10.1016/s0968-0896(01)00383-2

  日期：2002.4

  Members of the actinomycetes produce 1D-1-O-(2-[N-acetyl-L-cysteinyl]amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol or mycothiol 1 as principal low molecular mass thiol, Chemical synthesis of a biosynthetic precursor of mycothiol, the pseudodisaccharide 1D-1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol 13 was achieved by the following steps: (1) Enantioselcctive synthesis gave the glycosyl acceptors (-)-2,3,4,5,6-penta-O-acetyl-D-myo-inositol D-7 and the corresponding L-isomer L-7. (2) Condensation of D-7 and L-7 with the glycosyl donor 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-alpha-D-glucopyranosylbromide afforded the corresponding alpha and beta anomeric products, which could be resolved by silica gel chromatography, (3) Deprotection of these by hydrolysis using an anion exchange resin gave 1D- and 1L-1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol 13 and 15 and the corresponding beta-coupled anomers 14 and 16. Only 13, and to a much lesser extent 15, were used by enzymes present in an ammonium sulphate fraction of a cellfree extract of Mycobacterium smegmatis for the enzymatic synthesis of mycothiol. In the absence of acetyl-SCoA, the immediate biosynthetic precursor of 1, desacetylmycothiol, was the major product. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of 1-d- and 1-l-myo-inosityl 2-N-acetamido-2-deoxy-α-d-glucopyranoside establishes substrate specificity of the Mycobacterium tuberculosis enzyme AcGI deacetylase
  作者：Gillian M. Nicholas、Lisa L. Eckman、Pavol Kováč、Sarah Otero-Quintero、Carole A. Bewley

  DOI：10.1016/s0968-0896(03)00154-8

  日期：2003.6

  Mycothiol (MSH, 1-D-myo-inosityl 2-(N-acetyl-L-cysteinyl)amido-2-deoxy-alpha-D-glucopyrano side) is the principal low molecular weight thiol in actinomycetes. The enzyme 1-D-myo-inosityl 2-N-acetamido-2-deoxy-alpha-D-glucopyranoside deacetylase (AcGI deacetylase) is involved in the biosynthesis of MSH and forms the free amine 1-D-niyo-inosityl 2-amino-2-deoxy-alpha-D-glucopyranoside, which is used in the third of four steps of MSH biosynthesis. Here, we report the synthesis of two isomers of AcGL which contain either 1-L-myo-inositol or 1-D-myo-inositol. These synthetic products were used to investigate substrate specificity of the Mycobacterium tuberculosis enzyme AcGI deacetylase. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Synthesis of substrate analogues as potential inhibitors for Mycobacterium tuberculosis enzyme MshC
  作者：Krishnakant Patel、Fengling Song、Peter R. Andreana

  DOI：10.1016/j.carres.2017.10.014

  日期：2017.12

  promising target for developing new anti-mycobacterial compounds. Herein, we report on the synthesis of substrate analogues, as potential inhibitors, for the MshC enzyme. The target molecules were synthesized employing a Schmidt glycosylation strategy using an enantiomerically pure inositol acceptor and 2-deoxy trichloroacetimidate glycosyl donors with glycosylation yields greater than 70% and overall

  麦考硫醇半胱氨酸连接酶（MshC）是麦考硫醇（MSH）生物合成中的关键酶，也是开发新型抗分枝杆菌化合物的有希望的目标。在本文中，我们报道了作为MshC酶潜在抑制剂的底物类似物的合成。使用施密特糖基化策略，使用对映体纯的肌醇受体和2-脱氧三氯乙酰亚氨酸酯糖基供体，以糖基化收率大于70％且总收率＞ 5％来合成靶分子。肌醇受体是通过（±）-肌醇的手性拆分而获得的。
• Microbial products. 5. Absolute configuration of aminoglycoside X-14847
  作者：Hubert Maehr、Joanne M. Smallheer、John F. Blount

  DOI：10.1021/jo00315a029

  日期：1981.1