(R)-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropionic acid | 1190373-32-0

• 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
• 英文别名: (R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoic acid；(2R)-2-methyl-3-[(2S,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxypropanoic acid
• CAS: 1190373-32-0
• 化学式: C₃₈H₄₂O₈
• 分子量: 626.747
• InChiKey: ALLLOWYUKYCGCK-BEQUZSHXSA-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：

  (R)-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropionic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 51.5h， 生成 N-[(R)-3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyloxy)-2-methylpropanoyl]-(adamant-2-yl)glycyl-L-alanyl-D-isoglutamine
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New Mannose Derived Immunomodulating Adamantyltripeptides

  摘要：

  A novel class of mannosylated adamantyltripeptides, general formula of which is alpha-Man-OCH2CH(CH3)CO-AdGly-L-Ala-D-isoGln, were prepared, characterized, and their possible immunomodulatory properties investigated in some preliminary tests in vivo. All newly synthesized glycopeptides comprise in their structure the adamantylglycyl moiety linked to the dipeptide L-Ala-D-isoGln, as well as mannose. Adjuvant activity of mannosylated adamant-2-yl tripeptides was tested in the mouse model using ovalbumin as an antigen and in comparison to the peptidoglycan monomer (PGM, beta-D-GlcNAc-(1 -> 4)-D-MurNAc-L-Ala-D-isoGln-mesoDAP(epsilon NH2)-D-Ala-D-Ala). (doi: 10.5562/cca1827)

  DOI：

  10.5562/cca1827
• 作为产物：
  描述：

  (R)-methyl 3-(2,3,4,6-tetra-O-benzyl-α-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94%的产率得到(R)-(2,3,4,6-tetra-O-benzyl-α-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

• Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides
  作者：Rosana Ribić、Ranko Stojković、Lidija Milković、Mariastefania Antica、Marko Cigler、Srđanka Tomić

  DOI：10.3762/bjoc.15.174

  日期：——

  lipophilic adamantane on N- or C-terminus through a glycolyl or hydroxyisobutyryl linker. Adjuvant activities of synthesized compounds were investigated in the mouse model using ovalbumin as an antigen. Their activities were compared to the previously described mannosylated adamantane-containing desmuramyl peptide and peptidoglycan monomer. Tested compounds exhibited adjuvant activity and the strongest enhancement

  村酰二肽是具有佐剂性质的肽聚糖的最小结构。更换N-乙酰基村m基部分和亲脂性的增加是制备具有改善的药理学性质的mu基二肽类似物的重要方法。存在于免疫感受态细胞上的甘露糖受体是模式识别受体，通过甘露糖配体的结合，它们会影响免疫系统。在这里，我们介绍了新型甘露糖基去村酰胺肽衍生物的设计，合成和生物学评估。甘露糖通过乙醇酰基或羟基异丁酰基接头与在N-或C-末端上含有亲脂性金刚烷的二肽偶联。使用卵清蛋白作为抗原，在小鼠模型中研究了合成化合物的佐剂活性。将它们的活性与先前描述的含甘露糖基的金刚烷的去马甲酰肽和肽聚糖单体进行比较。21（Man-OCH 2 - ᴅ-（1-Ad）Gly-ʟ-Ala-ᴅ-isoGln）。
• Influence of Mannosylation on Immunostimulating Activity of Adamant-1-yl Tripeptide
  作者：Rosana Ribić、Lidija Habjanec、Ruža Frkanec、Branka Vranešić、Srđanka Tomić

  DOI：10.1002/cbdv.201200008

  日期：2012.7

  The mannosylated derivative of adamant-1-yl tripeptide (D-(Ad-1-yl)Gly-L-Ala-D-isoGln) was prepared to study the effects of mannosylation on adjuvant (immunostimulating) activity. Mannosylated adamant-1-yl tripeptide (Man-OCH(2) CH(Me)CO-D-(Ad-1-yl)Gly-L-Ala-D-isoGln) is a non-pyrogenic, H(2) O-soluble, and non-toxic compound. Adjuvant activity of mannosylated adamantyl tripeptide was tested in the

  制备金刚烷基-1-基三肽的甘露糖基化衍生物（D-（Ad-1-基）Gly-L-Ala-D-isoGln），以研究甘露糖基化对佐剂（免疫刺激）活性的影响。甘露糖基化的金刚烷基-1-基三肽（Man-OCH（2）CH（Me）CO-D-（Ad-1-yl）Gly-L-Ala-D-isoGln）是非热原的H（2）O可溶且无毒的化合物。在以卵清蛋白为抗原的小鼠模型中测试了甘露糖基化金刚烷基三肽的佐剂活性，并与亲本三肽和肽聚糖单体（PGM，β-D-GlcNAc-（1→4）-D-MurNAc-L-Ala- D-isoGln-mesoDAP（εNH（2））-D-Ala-D-Ala），一种众所周知的有效佐剂。金刚烷基三肽的甘露糖基化以与PGM相当的方式引起其免疫刺激活性的扩增。
• Design and syntheses of mono and multivalent mannosyl-lipoconjugates for targeted liposomal drug delivery
  作者：Adela Štimac、Jelena TrmĿiĿ Cvitaš、Leo Frkanec、Oliver Vugrek、Ruža Frkanec

  DOI：10.1016/j.ijpharm.2016.06.123

  日期：2016.9

  Multivalent mannosyl-lipoconjugates may be of interest for glycosylation of liposomes and targeted drug delivery because the mannose specifically binds to C-type lectin receptors on the particular cells. In this paper syntheses of two types of novel O-mannosides are presented. Conjugates 1 and 2 with a COOH-and NH2-functionalized spacer and the connection to a lysine and FmocNH-PEG-COOH, are described. The coupling reactions of prepared intermediates 6 and 4 with a PEGylated-DSPE or palmitic acid, respectively, are presented. Compounds 5, mono-, 8, di-and 12, tetravalent mannosyl-lipoconjugates, were synthesized. The synthesized compounds were incorporated into liposomes and liposomal preparations featuring exposed mannose units were characterized. Carbohydrate liposomal quartz crystal microbalance based assay has been established for studying carbohydrate-lectin binding. It was demonstrated that liposomes with incorporated mannosyl-lipoconjugates were effectively recognized by Con A and have great potential to be used for targeted liposomal drug delivery systems. (C) 2016 Elsevier B.V. All rights reserved.
• 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：——