5-amino-5-deoxy-α-D-ribose-1,2-cyclic phosphate | 1330004-15-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: 5-amino-5-deoxy-α-D-ribose-1,2-cyclic phosphate
• 英文别名: (3aR,5R,6R,6aR)-5-(aminomethyl)-2-hydroxy-2-oxo-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3,2]dioxaphosphol-6-ol
• CAS: 1330004-15-3
• 化学式: C₅H₁₀NO₆P
• 分子量: 211.111
• InChiKey: BYNSPSKNIZMFGN-TXICZTDVSA-N

物化性质

• 沸点：
  431.1±55.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.6
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  111
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-amino-5-deoxy-α-D-ribose-1,2-cyclic phosphate 、 邻苯二甲醛 在 ammonium acetate 作用下， 以 甲醇 、 乙醇 、 水 、 乙腈 为溶剂， 生成 5-(1-oxoisoindolinin-2-yl)-5-deoxy-α-D-ribose-1,2-cyclic phosphate
  参考文献：
  名称：

  Biosynthetic Origin and Mechanism of Formation of the Aminoribosyl Moiety of Peptidyl Nucleoside Antibiotics

  摘要：

  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.

  DOI：

  10.1021/ja206304k
• 作为产物：
  描述：

  5'-amino-5'-deoxyuridine 、 尿苷-5'-三磷酸 在 potassium phosphate 、 5'-amino-5'-deoxyuridine phosphorylase 、 UTP : 5-amino-5-deoxy-α-D-ribose-1-phosphate uridylyltransferase 、 magnesium chloride 作用下， 反应 3.0h， 生成 5-amino-5-deoxy-α-D-ribose-1,2-cyclic phosphate 、 尿苷5-单磷酸 、 尿嘧啶
  参考文献：
  名称：

  Biosynthetic Origin and Mechanism of Formation of the Aminoribosyl Moiety of Peptidyl Nucleoside Antibiotics

  摘要：

  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.

  DOI：

  10.1021/ja206304k