(R)-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyloxy)-2-methylpropionic acid | 1190373-45-5

• 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-β-D-mannopyranosyloxy)-2-methylpropionic acid
• 英文别名: (R)-3-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyloxy)-2-methylpropanoic acid；(2R)-2-methyl-3-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropanoic acid
• CAS: 1190373-45-5
• 化学式: C₃₈H₄₂O₈
• 分子量: 626.747
• InChiKey: ALLLOWYUKYCGCK-IMLWGXOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  46
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-羟基丁二酰亚胺 、 (R)-(2,3,4,6-tetra-O-benzyl-β-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78%的产率得到(R)-(2,3,4,6-tetra-O-benzyl-β-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
• 作为产物：
  描述：

  (R)-methyl 3-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyloxy)-2-methylpropanoate 在 水 、 sodium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以83%的产率得到(R)-(2,3,4,6-tetra-O-benzyl-β-D-mannopyranosyloxy)-2-methylpropionic acid
  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

文献信息

• Ribic, Rosana; Kovacevic, Monika; Petrovic-Perokovic, Vesna, Croatica Chemica Acta, 2010, vol. 83, # 4, p. 421 - 431
  作者：Ribic, Rosana、Kovacevic, Monika、Petrovic-Perokovic, Vesna、Gruic-Sovulj, Ita、Rapic, Vladimir、Tomic, Srdanka

  DOI：——

  日期：——