(R)-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropionic acid N-hydroxysuccinimide ester | 1190373-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropionic acid N-hydroxysuccinimide ester
• CAS: 1190373-33-1
• 化学式: C₄₂H₄₅NO₁₀
• 分子量: 723.82
• InChiKey: PTDIXRQIAQKROR-GLHVJAIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.94
• 重原子数：
  53.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  119.06
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (R)-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropionic acid N-hydroxysuccinimide ester 、 <2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-((D)-ethyl-1-carbonyl)-D-glucopyranose>-L-alanyl-D-isoglutaminyl-<(L)-meso-diaminopimeloyl-(D)-amide-(L)-D-alanyl-D-alanine> 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 49.0h， 生成 N-acetyl-β-D-glucosaminyl-(1->4)-N-acetylmuramyl-L-alanyl-D-iso-glutaminyl-{N(ε)-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]}-meso-2,6-diaminopimelyl-D-alanyl-D-alanine
  参考文献：
  名称：

  Novel mannosyl derivatives of peptidoglycan monomer: Synthesis and biological evaluation of immunomodulatory properties

  摘要：

  The aim of this work was to prepare mannosyl derivatives of peptidoglycan monomer (PGM, beta-D-GlcNAc( 1 -> 4)-D-MurNAc-L-Ala-D-isoGln-mesoDAP(epsilon NH(2))-D-Ala-D-Ala) in order to study the effects of mannosylation on adjuvant (immunostimulating) activity. Novel Man-OCH(2)CH(CH(3))CO-PGM isomers were substrates for N-acetylmuramyl-L-alanine amidase, like the parent PGM molecule. Adjuvant activity of Man-OCH(2)CH(CH(3)) CO-PGM was tested in the mouse model using ovalbumin as an antigen. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.016
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 (R)-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropionic acid 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以172.6 mg的产率得到(R)-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropionic acid N-hydroxysuccinimide ester
  参考文献：
  名称：

  Novel mannosyl derivatives of peptidoglycan monomer: Synthesis and biological evaluation of immunomodulatory properties

  摘要：

  The aim of this work was to prepare mannosyl derivatives of peptidoglycan monomer (PGM, beta-D-GlcNAc( 1 -> 4)-D-MurNAc-L-Ala-D-isoGln-mesoDAP(epsilon NH(2))-D-Ala-D-Ala) in order to study the effects of mannosylation on adjuvant (immunostimulating) activity. Novel Man-OCH(2)CH(CH(3))CO-PGM isomers were substrates for N-acetylmuramyl-L-alanine amidase, like the parent PGM molecule. Adjuvant activity of Man-OCH(2)CH(CH(3)) CO-PGM was tested in the mouse model using ovalbumin as an antigen. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.016