2-thio-D-glucose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-thio-D-glucose
• 英文别名: (3R,4S,5S,6R)-6-(hydroxymethyl)-3-mercaptotetrahydro-2H-pyran-2,4,5-triol；3-Deoxy-3-thio-glucose；(3R,4S,5S,6R)-6-(hydroxymethyl)-3-sulfanyloxane-2,4,5-triol
• 化学式: C₆H₁₂O₅S
• 分子量: 196.224
• InChiKey: PUWSGNUNXQAYLM-GASJEMHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  91.2
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 2-thio-D-glucose 在 5’-三磷酸腺苷 、 magnesium chloride 作用下， 反应 6.5h， 生成
  参考文献：
  名称：

  A Biosynthetic Pathway for BE-7585A, a 2-Thiosugar-Containing Angucycline-Type Natural Product

  摘要：

  Sulfur is an essential element found ubiquitously in living systems. However, there exist only a few sulfur-containing sugars in nature and their biosyntheses have not been studied. BE-7585A produced by Amycolatopsis orientalis subsp. vinearia BA-07585 has a 2-thiosugar and is a member of the angucycline class of compounds. We report herein the results of our initial efforts to study the biosynthesis of BE-7585A. Spectroscopic analyses verified the structure of BE-7585A, which is closely related to rhodonocardin A. Feeding experiments using C-13-labeled acetate were carried out to confirm that the angucycline core is indeed polyketide-derived. The results indicated an unusual manner of angular tetracyclic ring construction, perhaps via a Baeyer-Villiger type rearrangement. Subsequent cloning and sequencing led to the identification of the bex gene cluster spanning similar to 30 kbp. A total of 28 open reading frames, which are likely involved in BE-7585A formation, were identified in the cluster. In view of the presence of a homologue of a thiazole synthase gene (thiG), bexX, in the bex cluster, the mechanism of sulfur incorporation into the 2-thiosugar moiety could resemble that found in thiamin biosynthesis. A glycosyltransferase homologue, BexG2, was heterologously expressed in Escherichia coli. The purified enzyme successfully catalyzed the coupling of 2-thioglucose 6-phoshate and UDP-glucose to produce 2-thiotrehalose 6-phosphate, which is the precursor of the disaccharide unit in BE-7585A. On the basis of these genetic and biochemical experiments, a biosynthetic pathway for BE-7585A can now be proposed. The combined results set the stage for future biochemical studies of 2-thiosugar biosynthesis and BE-7585A assembly.

  DOI：

  10.1021/ja1014037

文献信息

• Compounds for use in polycystic kidney disease
  申请人：FONDAZIONE CENTRO SAN RAFFAELE OFFICE OF BIOTECHNOLOGY TRANSFER

  公开号：US10478446B2

  公开（公告）日：2019-11-19

  Polycystic kidney disease is a cystic genetic disorder of the kidneys. Recent identification of signaling cascades de-regulated in PKD has led to the initiation of several clinical trials, but an effective therapy is still lacking. A new therapeutic paradigm is capable of improving the proliferation rate and cystic kidney volume in PKD.

  多囊肾是一种肾脏囊性遗传疾病。最近发现的 PKD 信号级联失调导致了一些临床试验的启动，但仍然缺乏有效的治疗方法。一种新的治疗模式能够改善 PKD 的增殖率和囊性肾脏体积。
• MONOSACCHARIDE-BASED COMPOUNDS FOR THE TREATMENT OF PROLIFERATIVE AND INFLAMMATORY DERMATOLOGICAL DISEASES
  申请人：The University of Texas M.D. Anderson Cancer

  公开号：EP2663314A2

  公开（公告）日：2013-11-20
• COMPOUNDS FOR USE IN POLYCYSTIC KIDNEY DISEASE
  申请人：FONDAZIONE CENTRO SAN RAFFAELE OFFICE OF BIOTECHNOLOGY TRANSFER

  公开号：US20150297620A1

  公开（公告）日：2015-10-22

  Polycystic kidney disease is a cystic genetic disorder of the kidneys. Recent identification of signaling cascades de-regulated in PKD has led to the initiation of several clinical trials, but an effective therapy is still lacking. A new therapeutic paradigm is capable of improving the proliferation rate and cystic kidney volume in PKD.
• [EN] MONOSACCHARIDE-BASED COMPOUNDS FOR THE TREATMENT OF PROLIFERATIVE AND INFLAMMATORY DERMATOLOGICAL DISEASES<br/>[FR] COMPOSÉS À BASE DE MONOSACCHARIDES POUR LE TRAITEMENT DE MALADIES DERMATOLOGIQUES PROLIFÉRATIVES ET INFLAMMATOIRES
  申请人：INTERTECH BIO LLC

  公开号：WO2012097052A2

  公开（公告）日：2012-07-19

  The present invention relates to compounds and methods which may be useful as inhibitors of glycolysis, inhibitors of protein glycosylation, anti-virals, and down-regulators of insulin receptor and IGF- 1 receptor for the treatment or prevention of inflammatory dermatological diseases or proliferative dermatological diseases.
• [EN] METHOD OF TREATING VIRAL INFECTIONS WITH HEXOSE TYPE MONOSACCHARIDES AND ANALOGS THEREOF<br/>[FR] PROCÉDÉ DE TRAITEMENT D'INFECTIONS VIRALES AVEC DES MONOSACCHARIDES DE TYPE HEXOSES ET LEURS ANALOGUES
  申请人：UNIV TEXAS

  公开号：WO2021188586A1

  公开（公告）日：2021-09-23

  The present invention relates to methods of treating and preventing viral diseases and infections comprising the administration of hexoses and analogs and their prodrugs thereof that inhibit glycolysis and/or glycosylation.