L-alanyl-D-iso-glutaminyl-{N(ε)-[(R)-3-(α-D-mannopyranosyloxy)-2-methylpropanoyl]}-meso-2,6-diaminopimelyl-D-alanyl-D-alanine | 1190373-37-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: L-alanyl-D-iso-glutaminyl-{N(ε)-[(R)-3-(α-D-mannopyranosyloxy)-2-methylpropanoyl]}-meso-2,6-diaminopimelyl-D-alanyl-D-alanine
• CAS: 1190373-37-5
• 化学式: C₃₁H₅₄N₈O₁₅
• 分子量: 778.814
• InChiKey: OJWIRHDBWWQLDJ-BYZVMTCDSA-N

反应信息

• 作为产物：
  描述：

  N-acetyl-β-D-glucosaminyl-(1->4)-N-acetylmuramyl-L-alanyl-D-iso-glutaminyl-{N(ε)-[(R)-3-(α-D-mannopyranosyloxy)-2-methylpropanoyl]}-meso-2,6-diaminopimelyl-D-alanyl-D-alanine 在 human serum N-acetylmuramyl-L-alanine amidase 、 magnesium chloride 作用下， 反应 24.0h， 以91%的产率得到L-alanyl-D-iso-glutaminyl-{N(ε)-[(R)-3-(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