phenyl 2-O-(10-[2-naphthyl]-3,6,9-trioxadecanyl)-1-thio-β-D-galactopyranoside | 741677-89-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-(10-[2-naphthyl]-3,6,9-trioxadecanyl)-1-thio-β-D-galactopyranoside
• CAS: 741677-89-4
• 化学式: C₂₉H₃₆O₈S
• 分子量: 544.666
• InChiKey: SITBBOMOEJHZHV-LLQHYSMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  38.0
• 可旋转键数：
  15.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  106.84
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  phenyl 2-O-(10-[2-naphthyl]-3,6,9-trioxadecanyl)-1-thio-β-D-galactopyranoside 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， 反应 7.5h， 生成 3,4,6-tri-O-acetyl-2-O-(10-[2-naphthyl]-3,6,9-trioxadecanyl)-1-thio-β-D-galactopyranose
  参考文献：
  名称：

  Rational Design, Synthesis, and Characterization of Novel Inhibitors for Human β1,4-Galactosyltransferase

  摘要：

  An affinity labeling reagent, uridine 5'-(6-amino-{2-[(7-bromomethyl-2-naphthyl)methoxy-carbonylmethoxy]ethoxy}acetyl-6-deoxy-alpha-D-galactopyranosyl) diphosphate (1a), was designed on the basis of 3D docking simulation and synthesized to investigate the functional role of Trp310 residue located in the small loop near the active site of human recombinant galactosyltransferase (beta GalT-1). Mass spectrometric analysis revealed that the Trp310 residue of beta GalT1 can be selectively modified with the naphthylmethyl group of compound la at the C-3 position of the indole ring. This result motivated us to synthesize novel uridine-5'-diphosphogalactose (UDP-Gal) analogues as candidates for mechanism-based inhibitors for beta GalT-1. We found that uridine 5'-(6-O-[10-(2-naphthyl)-3,6,9-trioxadecanyl]-alpha-D-galactopyranosyl) diphosphate (2) is the strongest inhibitor (K-i = 1.86 mu M) against UDP-Gal (K-m = 4.91 mu M) among compounds reported previously. A cold spray ionization time-of-flight mass spectrometry study demonstrated that the complex of this inhibitor and beta GalT-1 cannot interact with an acceptor substrate in the presence of Mn2+.

  DOI：

  10.1021/jm0504297
• 作为产物：
  描述：

  1-chloro-10-(2-naphthyl)-3,6,9-trioxadecane 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 phenyl 2-O-(10-[2-naphthyl]-3,6,9-trioxadecanyl)-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Rational Design, Synthesis, and Characterization of Novel Inhibitors for Human β1,4-Galactosyltransferase

  摘要：

  An affinity labeling reagent, uridine 5'-(6-amino-{2-[(7-bromomethyl-2-naphthyl)methoxy-carbonylmethoxy]ethoxy}acetyl-6-deoxy-alpha-D-galactopyranosyl) diphosphate (1a), was designed on the basis of 3D docking simulation and synthesized to investigate the functional role of Trp310 residue located in the small loop near the active site of human recombinant galactosyltransferase (beta GalT-1). Mass spectrometric analysis revealed that the Trp310 residue of beta GalT1 can be selectively modified with the naphthylmethyl group of compound la at the C-3 position of the indole ring. This result motivated us to synthesize novel uridine-5'-diphosphogalactose (UDP-Gal) analogues as candidates for mechanism-based inhibitors for beta GalT-1. We found that uridine 5'-(6-O-[10-(2-naphthyl)-3,6,9-trioxadecanyl]-alpha-D-galactopyranosyl) diphosphate (2) is the strongest inhibitor (K-i = 1.86 mu M) against UDP-Gal (K-m = 4.91 mu M) among compounds reported previously. A cold spray ionization time-of-flight mass spectrometry study demonstrated that the complex of this inhibitor and beta GalT-1 cannot interact with an acceptor substrate in the presence of Mn2+.

  DOI：

  10.1021/jm0504297