5'-O-(5''-amino-5''-deoxy-β-D-ribosyl)uridine | 302917-20-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5'-O-(5''-amino-5''-deoxy-β-D-ribosyl)uridine
• 英文别名: 1-[(2R,3R,4S,5R)-5-((2R,3R,4S,5R)-5-Aminomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione；1-[(2R,3R,4S,5R)-5-[[(2R,3R,4S,5R)-5-(aminomethyl)-3,4-dihydroxyoxolan-2-yl]oxymethyl]-3,4-dihydroxyoxolan-2-yl]pyrimidine-2,4-dione
• CAS: 302917-20-0
• 化学式: C₁₄H₂₁N₃O₉
• 分子量: 375.335
• InChiKey: JGQGGIXOLDAQPJ-JXHPLLHESA-N

物化性质

• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  184
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5'-O-(5''-amino-5''-deoxy-β-D-ribosyl)uridine 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 1-[(2R,3R,4S,5R)-5-((2R,3R,4S,5R)-5-Aminomethyl-3,4-dihydroxy-tetrahydro-furan-2-yloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-dihydro-pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of analogues of the O-β-d-Ribofuranosyl Nucleoside Moiety of Liposidomycins. Part 1: contribution of the amino group and the Uracil Moiety upon the inhibition of MraY

  摘要：

  The O-beta -D-ribofuranosyl nucleoside I is the minimal structural entity of liposidomycins maintaining enzyme inhibitory activity. Modifications performed on both the primary amine and the uracil moieties clearly demonstrate their major contribution to the inhibition of the bacterial translocase (MraY). (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00715-0
• 作为产物：
  描述：

  四乙酰核糖 在 甲醇 、 氯化亚砜 、 sodium azide 、 氨 、 水 、 氰化汞 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 三苯基膦 、 丙酮 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 149.0h， 生成 5'-O-(5''-amino-5''-deoxy-β-D-ribosyl)uridine
  参考文献：
  名称：

  Synthesis of the Nucleoside Moiety of Liposidomycins: Elucidation of the Pharmacophore of this Family of MraY Inhibitors

  摘要：

  Tunicamycins (TCMs) and liposidomycins (LPMs) are naturally occurring inhibitors of the bacterial translocase (MraY). Based on structure-activity relationship (SAR) studies, a molecular model has been proposed for their inhibitory mechanism. This study points out the importance of the nucleoside moiety of liposidomycins in the inhibition of MraY. A simplified molecule (I) based on the liposidomycin core structure has been synthesised and tested on MraY. The compound displayed a moderate inhibitory activity (IC50-50 mu M). The validation of the molecular model was then performed by synthesising higher homologues of I, containing an additional stereocentre in the 5' position (XIV and XV). In agreement with the prediction, only the (S) isomer XV showed significant activity against MraY (IC50=5 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00349-8

文献信息

• Biosynthetic Origin and Mechanism of Formation of the Aminoribosyl Moiety of Peptidyl Nucleoside Antibiotics
  作者：Xiuling Chi、Pallab Pahari、Koichi Nonaka、Steven G. Van Lanen

  DOI：10.1021/ja206304k

  日期：2011.9.14

  Several peptidyl nucleoside antibiotics that inhibit bacterial translocase I involved in peptidoglycan cell wall biosynthesis contain an aminoribosyl moiety, an unusual sugar appendage in natural products. We present here the delineation of the biosynthetic pathway for this moiety upon in vitro characterization of four enzymes (LipM-P) that are functionally assigned as (i) LipO, an L-methionine:uridine-5'-aldehyde aminotransferase; (ii) LipP, a 5'-amino-5'-deoxyuridine phosphorylase; LipM, a UTP:5-amino-5-deoxy-alpha-D-ribose-1-phosphate uridylyltransferase; and (iv) LipN, a 5-amino-5-deoxyribosyltransferase. The cumulative results reveal a unique ribosylation pathway that is highlighted by, among other features, uridine-5'-monophosphate as the source of the sugar, a phosphorylase strategy to generate a sugar-1-phosphate, and a primary amine-requiring nucleotidylyltransferase that generates the NDP-sugar donor.
• Synthesis of analogues of the O-β-d-Ribofuranosyl Nucleoside Moiety of Liposidomycins. Part 1: contribution of the amino group and the Uracil Moiety upon the inhibition of MraY
  作者：C Dini、N Drochon、S Feteanu、J.C Guillot、C Peixoto、J Aszodi

  DOI：10.1016/s0960-894x(00)00715-0

  日期：2001.2

  The O-beta -D-ribofuranosyl nucleoside I is the minimal structural entity of liposidomycins maintaining enzyme inhibitory activity. Modifications performed on both the primary amine and the uracil moieties clearly demonstrate their major contribution to the inhibition of the bacterial translocase (MraY). (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of the Nucleoside Moiety of Liposidomycins: Elucidation of the Pharmacophore of this Family of MraY Inhibitors
  作者：C. Dini、P. Collette、N. Drochon、J.C. Guillot、G. Lemoine、P. Mauvais、J. Aszodi

  DOI：10.1016/s0960-894x(00)00349-8

  日期：2000.8

  Tunicamycins (TCMs) and liposidomycins (LPMs) are naturally occurring inhibitors of the bacterial translocase (MraY). Based on structure-activity relationship (SAR) studies, a molecular model has been proposed for their inhibitory mechanism. This study points out the importance of the nucleoside moiety of liposidomycins in the inhibition of MraY. A simplified molecule (I) based on the liposidomycin core structure has been synthesised and tested on MraY. The compound displayed a moderate inhibitory activity (IC50-50 mu M). The validation of the molecular model was then performed by synthesising higher homologues of I, containing an additional stereocentre in the 5' position (XIV and XV). In agreement with the prediction, only the (S) isomer XV showed significant activity against MraY (IC50=5 mu M). (C) 2000 Elsevier Science Ltd. All rights reserved.