UDP-beta-L-rhamnose(2-)

• 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: UDP-beta-L-rhamnose(2-)
• 英文别名: [[(2R,3S,4R,5R)-5-(2,4-dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-oxidophosphoryl] [(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl] phosphate
• 化学式: C15H22N2O16P2-2
• 分子量: 548.29
• InChiKey: DRDCJEIZVLVWNC-SLBWPEPYSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  -6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  277
• 氢给体数：
  6
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  soyasaponin III(1-) 、 UDP-beta-L-rhamnose(2-) 生成 氢(+1)阳离子 、 soyasaponin I(1-) 、 UDP
  参考文献：
  名称：

  Identification and characterization of glycosyltransferases involved in the biosynthesis of soyasaponin I inGlycine max

  摘要：

  Triterpene saponins are a diverse group of compounds with a structure consisting of a triterpene aglycone and sugars. Identification of the sugar‐transferase involved in triterpene saponin biosynthesis is difficult due to the structural complexity of triterpene saponin. Two glycosyltransferases from Glycine max, designated as GmSGT2 and GmSGT3, were identified and characterized. In vitro analysis revealed that GmSGT2 transfers a galactosyl group from UDP‐galactose to soyasapogenol B monoglucuronide, and that GmSGT3 transfers a rhamnosyl group from UDP‐rhamnose to soyasaponin III. These results suggest that soyasaponin I is biosynthesized from soyasapogenol B by successive sugar transfer reactions.

  DOI：

  10.1016/j.febslet.2010.03.037
• 作为产物：
  描述：

  氢(+1)阳离子 、 NADPH(4-) 、 UDP-4-dehydro-beta-L-rhamnose 生成 NADP⁺ 、 UDP-beta-L-rhamnose(2-)
  参考文献：
  名称：

  Functional Analysis of Arabidopsis thaliana RHM2/MUM4, a Multidomain Protein Involved in UDP-D-glucose to UDP-L-rhamnose Conversion

  摘要：

  UDP-L-rhamnose is required for the biosynthesis of cell wall rhamnogalacturonan-I, rhamnogalacturonan-II, and natural compounds in plants. It has been suggested that the RHM2/MUM4 gene is involved in conversion of UDP-D-glucose to UDP-L-rhamnose on the basis of its effect on rhamnogalacturonan-l-directed development in Arabidopsis thaliana. RHM2/MUM4-related genes, RHM1 and RHM3, can be found in the A. thaliana genome. Here we present direct evidence that all three RHM proteins have UDP-D-glucose 4,6-dehydratase, UDP-4-keto-6-deoxy-D-glucose 3,5-epimerase, and UDP-4-keto-Lrhamnose 4-keto-reductase activities in the cytoplasm when expressed in the yeast Saccharomyces cerevisiae. Functional domain analysis revealed that the N-terminal region of RHM2 (RHM2-N; amino acids 1-370) has the first activity and the C-terminal region of RHM2 (RHM2-C; amino acids 371-667) has the two following activities. This suggests that RHM2 converts UDP-D-glucose to UDP-L-rhamnose via an UDP-4-keto-6-deoxy-D-glucose intermediate. Site-directed mutagenesis of RHM2 revealed that mucilage defects in MUM4-1 and MUM4-2 mutant seeds of A. thaliana are caused by abolishment of RHM2 enzymatic activity in the mutant strains and furthermore, that the GXXGXX(G/A) and YXXXK motifs are important for enzymatic activity. Moreover, a kinetic analysis of purified His(6)-tagged RHM2-N protein revealed 5.9-fold higher affinity of RHM2 for UDP-D-glucose than for dTDP-D-glucose, the preferred substrate for dTDP-D-glucose 4,6-dehydratase from bacteria. RHM2-N activity is strongly inhibited by UDP-L-rhamnose, UDP-D-xylose, and UDP but not by other sugar nucleotides, suggesting that RHM2 maintains cytoplasmic levels of UDP-D-glucose and UDP-L-rhamnose via feedback inhibition by UDP-L-rhamnose and UDP-D-xylose.

  DOI：

  10.1074/jbc.m610196200

文献信息

• Biochemical characterization of rhamnosyltransferase involved in biosynthesis of pectic rhamnogalacturonan I in plant cell wall
  作者：Yohei Uehara、Shunsuke Tamura、Yusuke Maki、Kenta Yagyu、Tadashi Mizoguchi、Hitoshi Tamiaki、Tomoya Imai、Tadashi Ishii、Takao Ohashi、Kazuhito Fujiyama、Takeshi Ishimizu

  DOI：10.1016/j.bbrc.2017.03.012

  日期：2017.4

  The pectin in plant cell walls consists of three domains: homogalacturonan, rhamnogalacturonan (RG)-I, and RG-II. It is predicted that around 50 different glycosyltransferases are required for their biosynthesis. Among these, the activities of only a few glycosyltransferases have been detected because pectic oligosaccharides are not readily available for use as substrates. In this study, fluorogenic

  植物细胞壁中的果胶由三个结构域组成：高半乳糖醛酸聚糖，鼠李糖半乳糖醛酸聚糖（RG）-I和RG-II。据预测，它们的生物合成需要大约50种不同的糖基转移酶。其中，由于果胶寡糖不易用作底物，因此仅检测到少数糖基转移酶的活性。在本研究中，制备了具有3-14个聚合度（DP）的荧光吡啶基化RG-1骨干低聚糖（PA-RGs）。使用这些寡糖，从小豆表皮胚轴的微粒体中检测到涉及RG-1主链二糖基重复单元（-4GalUAα1-2Rhaα1-）生物合成的RG-1鼠李糖基转移酶（RRT）的活性。发现RRT首选更长的受体底物，DP> 7的PA-RG。而且它不需要任何金属离子来发挥作用。RRT位于高尔基体和内质网。RRT的活性与上胚轴生长相吻合，表明RG-1生物合成参与了植物的生长。
• Regioselective synthesis of flavonoid bisglycosides using Escherichia coli harboring two glycosyltransferases
  作者：Hyeon Jeong Kim、Bong-Gyu Kim、Joong-Hoon Ahn

  DOI：10.1007/s00253-013-4844-7

  日期：2013.6

  as sugar acceptors. Quercetin rhamnosides contain antiviral activity. Two quercetin diglycosides, quercetin 3-O-glucoside-7-O-rhamnoside and quercetin 3,7-O-bisrhamnoside, were synthesized using Escherichia coli expressing two UGTs. For the synthesis of quercetin 3-O-glucoside-7-O-rhamnoside, AtUGT78D2, which transfers glucose from UDP-glucose to the 3-hydroxyl group of quercetin, and AtUGT89C1, which

  由于类黄酮中存在多个羟基，因此不容易实现类黄酮的区域选择性糖基化。通过使用尿苷二磷酸依赖性糖基转移酶（UGT）可以克服这一障碍，该酶使用核苷酸糖作为糖供体，并使用包括类黄酮在内的多种化合物作为糖受体。槲皮素鼠李糖苷具有抗病毒活性。使用表达两个UGT的大肠杆菌合成了两种槲皮素二糖苷，槲皮素3-O-葡糖苷-7-O-鼠李糖苷和槲皮素3,7-O-双鼠李糖苷。对于槲皮素3-O-葡萄糖苷-7-O-鼠李糖苷的合成，AtUGT78D2将葡萄糖从UDP-葡萄糖转移到槲皮素的3-羟基，而AtUGT89C1将鼠李糖从UDP-鼠李糖转移到7-羟基。一组槲皮素3-O-葡萄糖苷，被转化到大肠杆菌中。使用这种方法，合成了67 mg / L槲皮素3-O-葡萄糖苷-7-O-鼠李糖苷。对于槲皮素3,7-O-双鼠李糖苷的合成，使用将鼠李糖转移至槲皮素3-羟基的AtUGT78D1和AtUGT89C1。共表达拟南芥的RHM2基因以
• Discovery of UDP-Glycosyltransferases and BAHD-Acyltransferases Involved in the Biosynthesis of the Antidiabetic Plant Metabolite Montbretin A
  作者：Sandra Irmisch、Seohyun Jo、Christopher R. Roach、Sharon Jancsik、Macaire Man Saint Yuen、Lufiani L. Madilao、Mark O’Neil-Johnson、Russel Williams、Stephen G. Withers、Joerg Bohlmann

  DOI：10.1105/tpc.18.00406

  日期：2018.8

  active molecules for drug discovery. The acylated flavonol glycoside montbretin A (MbA) and its precursor myricetin 3-O-(6'-O-caffeoyl)-glucosyl rhamnoside (mini-MbA) are potent inhibitors of human pancreatic α-amylase and are being developed as drug candidates to treat type-2 diabetes. MbA occurs in corms of the ornamental plant montbretia (Crocosmia x crocosmiiflora), but a system for large-scale MbA production

  植物专门的代谢是药物发现的生物活性分子的丰富资源。酰化黄酮醇糖苷 montbretin A (MbA) 及其前体杨梅素 3-O-(6'-O-咖啡酰基)-葡萄糖基鼠李糖苷 (mini-MbA) 是人胰腺 α-淀粉酶的有效抑制剂，正在开发作为候选药物治疗2型糖尿病。 MbA 存在于观赏植物 montbretia (Crocosmia x crocosmiiflora) 的球茎中，但目前尚无大规模生产 MbA 的系统。来自黄酮醇杨梅素的 MbA 生物合成和 MbA 积累发生在球茎发育的早期阶段。我们建立了杨梅素 3-O-鼠李糖苷 (MR)、杨梅素 3-O-葡萄糖基鼠李糖苷 (MRG) 和 mini-MbA 作为 MbA 生物合成的前三种中间体。对比年轻和年老球茎的转录组揭示了UDP糖依赖性糖基转移酶（UGT）和BAHD-酰基转移酶（BAHD-AT）的差异表达。 UGT77B2和UGT709G2分
• UGT73C6 and UGT78D1, Glycosyltransferases Involved in Flavonol Glycoside Biosynthesis in Arabidopsis thaliana
  作者：Patrik Jones、Burkhard Messner、Jun-Ichiro Nakajima、Anton R. Schäffner、Kazuki Saito

  DOI：10.1074/jbc.m303523200

  日期：2003.11

  Flavonol glycosides constitute one of the most prominent plant natural product classes that accumulate in the model plant Arabidopsis thaliana. To date there are no reports of functionally characterized flavonoid glycosyltransferases in Arabidopsis, despite intensive research efforts aimed at both flavonoids and Arabidopsis. In this study, flavonol glycosyltransferases were considered in a functional genomics approach aimed at revealing genes involved in determining the flavonol-glycoside profile. Candidate glycosyltransferase-encoding genes were selected based on homology to other known flavonoid glycosyltransferases and two T-DNA knockout lines lacking flavonol-3-O-rhamnoside-7-O-rhamnosides (ugt78D1) and quercetin-3-O-rhamnoside-7-O-glucoside (ugt73C6 and ugt78D1) were identified. To confirm the in planta results, cDNAs encoding both UGT78D1 and UGT73C6 were expressed in vitro and analyzed for their qualitative substrate specificity. UGT78D1 catalyzed the transfer of rhamnose from UDP-rhamnose to the 3-OH position of quercetin and kaempferol, whereas UGT73C6 catalyzed the transfer of glucose from UDPglucose to the 7-OH position of kaempferol-3-O-rhamnoside and quercetin-3-O-rhamnoside, respectively. The present results suggest that UGT78D1 and UGT73C6 should be classified as UDP-rhamnose:flavonol-3-O-rhamnosyltransferase and UDP-glucose:flavonol-3-O-glycoside-7-O-glucosyltransferase, respectively.
• Bar-Peled M.; Lewinsohn E.; Fluhr R., J Biol Chem, 1991, 0021-9258, 20953-9
  作者：Bar-Peled M.、Lewinsohn E.、Fluhr R.、Gressel J.

  DOI：——

  日期：——