TDP-L-rhamnose | 16268-29-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷酸
• 英文名称: TDP-L-rhamnose
• 英文别名: dTDP-alpha-L-rhamnose；[hydroxy-[[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy]phosphoryl] [(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] hydrogen phosphate
• CAS: 16268-29-4
• 化学式: C₁₆H₂₆N₂O₁₅P₂
• 分子量: 548.334
• InChiKey: ZOSQFDVXNQFKBY-GPNJKSCQSA-N

物化性质

• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.8
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  251
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  TDP-L-rhamnose 、 白杨素 在 flavonol 7-O-rhamnosyltransferase from Arabidopsis thaliana 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Expanded acceptor substrates flexibility study of flavonol 7-O-rhamnosyltransferase, AtUGT89C1 from Arabidopsis thaliana

  摘要：

  Acceptor substrates flexibility of previously characterized flavonol 7-O-rhamnosyltransferase (AtUGT89C1) from Arabidopsis thaliana was explored with an endogenous nucleotide diphosphate sugar and five different classes of flavonoids (flavonols, flavones, flavanones, chalcone and stilbenes) through a biotransformation approach. In contrast to the previous reports, this study highlights the expanded acceptor substrate promiscuity of AtUGT89C1 for the regiospecific glycosylation of diverse class of flavonoids at 7-hydroxyl position using microbial thymidine diphosphate (TDP)-L-rhamnose as sugar donor instead of uridine diphosphate-L-rhamnose. We examine the biocatalytic potential of AtUGT89C1 using endogenous sugar (TDP-L-rhamnose) from E. coli to generate a library of flavonoid 7-O-rhamnosides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2015.09.010
• 作为产物：
  描述：

  胸苷酸 、 对氟苯甲醇 在 乙酰磷酸 、 乙酸激酶(-20℃) 、 thymidine monophosphate kinase 、 β-烟酰胺腺嘌呤二核苷酸 、 5’-三磷酸腺苷 、 magnesium chloride 作用下， 以 aq. phosphate buffer 为溶剂， 反应 8.0h， 生成 TDP-L-rhamnose
  参考文献：
  名称：

  两种双功能酶在抗肿瘤抗生素光神霉素脱氧糖的生物合成和附着中的协同作用

  摘要：

  两种双功能酶协同组装和定位抗癌抗生素光神霉素的两种糖，D-橄榄糖和D- mycarose。MtmC 根据支持的 MtmGIV 活动完成两种糖构建块的生物合成。MtmGIV 将这两种糖转移到两种结构不同的受体底物上。这些酶的双重功能解释了两种基本但以前未识别的活动。

  DOI：

  10.1002/anie.201205414

文献信息

• Two Trifunctional Leloir Glycosyltransferases as Biocatalysts for Natural Products Glycodiversification
  作者：Ramesh Prasad Pandey、Puspalata Bashyal、Prakash Parajuli、Tokutaro Yamaguchi、Jae Kyung Sohng

  DOI：10.1021/acs.orglett.9b03040

  日期：2019.10.4

  activity of 20 different classes of 59 structurally different natural and non-natural products. Both enzymes transferred various sugars at three nucleophilic groups (OH, NH2, SH) of diverse compounds to produce O-, N-, and S-glycosides. The enzymes also displayed a catalytic reversibility potential for a one-pot transglycosylation, thus bestowing a cost-effective application in biosynthesis of glycodiversified

  两种混杂的地衣芽孢杆菌糖基转移酶YdhE和YojK表现出20种不同类别的59种结构不同的天然和非天然产物的突出的立体特异性但非区域特异性的糖基化活性。两种酶都在各种化合物的三个亲核基团（OH，NH 2，SH）上转移了各种糖，从而生成O-，N-和S-糖苷。这些酶还显示了一锅转糖基化的催化可逆性潜力，因此在药物发现中赋予了糖多样化天然产物生物合成的经济有效应用。
• Expanded acceptor substrates flexibility study of flavonol 7-O-rhamnosyltransferase, AtUGT89C1 from Arabidopsis thaliana
  作者：Prakash Parajuli、Ramesh Prasad Pandey、Nguyen Thi Huyen Trang、Tae Jin Oh、Jae Kyung Sohng

  DOI：10.1016/j.carres.2015.09.010

  日期：2015.12

  Acceptor substrates flexibility of previously characterized flavonol 7-O-rhamnosyltransferase (AtUGT89C1) from Arabidopsis thaliana was explored with an endogenous nucleotide diphosphate sugar and five different classes of flavonoids (flavonols, flavones, flavanones, chalcone and stilbenes) through a biotransformation approach. In contrast to the previous reports, this study highlights the expanded acceptor substrate promiscuity of AtUGT89C1 for the regiospecific glycosylation of diverse class of flavonoids at 7-hydroxyl position using microbial thymidine diphosphate (TDP)-L-rhamnose as sugar donor instead of uridine diphosphate-L-rhamnose. We examine the biocatalytic potential of AtUGT89C1 using endogenous sugar (TDP-L-rhamnose) from E. coli to generate a library of flavonoid 7-O-rhamnosides. (C) 2015 Elsevier Ltd. All rights reserved.
• Cooperation of Two Bifunctional Enzymes in the Biosynthesis and Attachment of Deoxysugars of the Antitumor Antibiotic Mithramycin
  作者：Guojun Wang、Pallab Pahari、Madan K. Kharel、Jing Chen、Haining Zhu、Steven G. Van Lanen、Jürgen Rohr

  DOI：10.1002/anie.201205414

  日期：2012.10.15

  Two bifunctional enzymes cooperate in the assembly and the positioning of two sugars, D‐olivose and D‐mycarose, of the anticancer antibiotic mithramycin. MtmC finishes the biosynthesis of both sugar building blocks depending on which MtmGIV activity is supported. MtmGIV transfers these two sugars onto two structurally distinct acceptor substrates. The dual function of these enzymes explains two essential

  两种双功能酶协同组装和定位抗癌抗生素光神霉素的两种糖，D-橄榄糖和D- mycarose。MtmC 根据支持的 MtmGIV 活动完成两种糖构建块的生物合成。MtmGIV 将这两种糖转移到两种结构不同的受体底物上。这些酶的双重功能解释了两种基本但以前未识别的活动。