benzyl D-isoglutaminate hydrochloride | 18800-75-4

• 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: benzyl D-isoglutaminate hydrochloride
• 英文别名: D-isoglutamine benzyl ester hydrochloride；D-γ-methyl isoglutamine hydrochloride；benzyl (4R)-4,5-diamino-5-oxopentanoate;hydrochloride
• CAS: 18800-75-4
• 化学式: C₁₂H₁₆N₂O₃*ClH
• 分子量: 272.732
• InChiKey: HSXVFJRDTASLQJ-HNCPQSOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.74
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  benzyl D-isoglutaminate hydrochloride 在 N-甲基吗啉 、 盐酸 、 溶剂黄146 、 氯甲酸异丁酯 作用下， 以 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 4.67h， 生成 benzyl N²-(N-acetyl-1-O-benzyl-α-D-muramoyl)-L-alanyl-D-isoglutaminate
  参考文献：
  名称：

  N 2-（N-乙酰基-6- O-硬脂酰基-α-D-村酰胺基）-L-丙氨酰基-D-异谷氨酰胺的合成及光谱表征

  摘要：

  标题化合物1是通过公开的途径合成的，必须对其进行修饰（从容易获得的起始原料开始，需要七个步骤）。1的表征通过光谱方法（FAB-MS，1 H-NMR，包括2D-COSY）实现。此外，购买用于比较的市售参考材料明确确定为10，即未完全脱保护1。

  DOI：

  10.1002/hlca.19930760819
• 作为产物：
  描述：

  (R)-benzyl 5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate 、 、 盐酸 、 乙醚 以 乙酸乙酯 为溶剂， 反应 0.17h， 以to give benzyl D-isoglutaminate hydrochloride (5, n = 2) which的产率得到benzyl D-isoglutaminate hydrochloride
  参考文献：
  名称：

  Novel immunological adjuvant compounds and methods of preparation thereof

  摘要：

  本申请涉及一种新型免疫佐剂化合物，其化学式为：##STR1## 其中R和R.sup.1各自相同或不同，可以是氢或酰基基团；R.sup.2是未取代或取代的烷基基团，或未取代或取代的芳基基团；R.sup.6是烷基基团，X是氨基酰基基团；Y是D-异天冬酰胺或D-异谷氨酰胺。

  公开号：

  US04082736A1

文献信息

• [EN] SYNTHETIC N-ACETYL-MURAMIC ACID DERIVATIVES AND USES THEREOF<br/>[FR] DÉRIVÉS D'ACIDE MURAMIQUE N-ACÉTYLÉ SYNTHÉTIQUES ET LEURS UTILISATIONS
  申请人：UNIV DELAWARE

  公开号：WO2016172615A1

  公开（公告）日：2016-10-27

  The present invention provides N-acetyl-muramic acid (NAM) derivatives having Formula I, wherein Xa is selected from the group consisting of X1-X59, Ya is selected from the group consisting of H, monophosphate, uridine diphosphate and ethyl azide linker prepared from 2-azido-ethanol, and Za is selected from the group consisting of OH, an ethylene diamine coupled fluorophore, a peptide and a peptide with an ethylene diamine coupled fluorophore, wherein the peptide is selected from the group consisting of a monopeptide, a dipeptide, a tripeptide and a pentapeptide. Also provided are methods for synthesizing NAM derivatives and methods for modulating Nod2 in cells, modifying bacterial cell wall or modulating innate immune response by a subject to bacterial cells upon exposure to NAM derivatives.

  本发明提供具有式I的N-乙酰-壳聚糖酸（NAM）衍生物，其中Xa选自X1-X59组，Ya选自H、磷酸单酯、尿苷二磷酸和由2-叠氮乙醇制备的乙基叠氮连接剂组，Za选自OH、乙二胺偶联的荧光素、肽和乙二胺偶联的肽，其中肽选自单肽、二肽、三肽和五肽组。还提供了合成NAM衍生物的方法以及通过暴露于NAM衍生物后调节细胞中Nod2、修改细菌细胞壁或调节受试者对细菌细胞的固有免疫反应的方法。
• N-acyldipeptides, processes for the preparation thereof and
  申请人：——

  公开号：US05514654A1

  公开（公告）日：1996-05-07

  N-acyldipeptides of formula I ##STR1## wherein R represents a rest of formula ##STR2## and R.sub.4, Y, m, n and Z have the meaning as defined in the description, R.sub.1 represents hydrogen, a 1-10 C. alkyl, an optionally substituted methyl or benzyl, R.sub.2 represents a --CO--A group, wherein A has the meanings as defined in the description, R.sub.3 represents a --(CH.sub.2).sub.p --CO--W group, wherein p and W have the meaning as defined in the description.

  公式I的N-酰基二肽，其中R代表公式中的余项，R.sub.4、Y、m、n和Z的含义如描述中定义，R.sub.1代表氢、1-10碳的烷基、可选取代的甲基或苄基，R.sub.2代表一个--CO--A基团，其中A的含义如描述中定义，R.sub.3代表一个--(CH.sub.2).sub.p--CO--W基团，其中p和W的含义如描述中定义。
• Chemical Synthesis of<i>N</i>-Acetylmuramyl Peptides with Partial Structures of Bacterial Cell Wall and Their Analogs in Relation to Immunoadjuvant Activities
  作者：Shoichi Kusumoto、Yuzo Tarumi、Kazuhiro Ikenaka、Tetsuo Shiba

  DOI：10.1246/bcsj.49.533

  日期：1976.2

  in Staphylococcus aureus were synthesized in order to elucidate the minimum effective structure responsible for immunoadjuvant activity of bacterial cell walls. In view of the finding that N-acetylmuramyl-L-alanyl-D-isoglutamine was the least structure moiety for exhibition of the activity, nine analogs of either N-acetylmuramyl amino acid or N-acetylmuramyl dipeptide were also synthesized.

  为了阐明负责细菌细胞壁免疫佐剂活性的最小有效结构，合成了对应于金黄色葡萄球菌细胞壁部分结构的连续长度的 N-乙酰胞壁酰肽。鉴于发现 N-乙酰胞壁酰-L-丙氨酰-D-异谷氨酰胺是表现活性最少的结构部分，还合成了 N-乙酰胞壁酰氨基酸或 N-乙酰胞壁酰二肽的九种类似物。
• Syntheses of Several Muramyl Peptides in Relation to Chemical Structures of Less Immunoadjuvant Bacterial Cell Walls
  作者：Shoichi Kusumoto、Kazuhiro Ikenaka、Tetsuo Shiba

  DOI：10.1246/bcsj.52.1665

  日期：1979.6

  Various structural analogs of N-acetylmuramyl-l-alanyl-d-isoglutamine, which had been shown to be the minimum structure required for the immunoadjuvant activity of bacterial cell walls, were synthesized in order to investigate in more detail the relationship between the activity and chemical structures. Particularly, the compounds of the structures corresponding to the cell walls of special bacteria without immunoadjuvant activity were prepared in this study. Several novel procedures including the preparation of a branched glutamyl peptide were newly exploited to accomplish the syntheses of muramyl peptides with complicated structures. As a result of this synthetic study, new informations were obtained on the structural requirement for the immunoadjucant activity.

  N-acetylmuramyl-l-alanyl-d-isoglutamine 是细菌细胞壁具有免疫佐剂活性所需的最小结构，为了更详细地研究这种活性与化学结构之间的关系，我们合成了 N-acetylmuramyl-l-alanyl-d-isoglutamine 的各种结构类似物。本研究特别制备了与无免疫佐剂活性的特殊细菌细胞壁结构相对应的化合物。本研究还采用了包括制备支链谷氨酰肽在内的几种新方法，合成了结构复杂的氨甲酰肽。通过这项合成研究，我们获得了有关免疫佐剂活性结构要求的新信息。
• Modulation of cytokine production by some phthalimido-desmuramyl dipeptides and their cytotoxicity
  作者：Stanislav Gobec、Marija Sollner-Dolenc、Uroš Urleb、Branka Wraber、Saša Simčič、Metka Filipič

  DOI：10.1016/j.farmac.2004.01.003

  日期：2004.5

  Muramyl dipeptide (MDP) is the smallest bacterial cell wall peptidoglycan component having immunomodulatory activity. In an attempt to obtain MDP derivatives with improved and better defined pharmacological profiles we synthesized a new lipophilic phthalimido-desmuramyl dipeptide, LK 508. This novel MDP analogue and three structurally related phthalimido-desmuramyl dipeptides (LK 413, LK 511 and LK 512) were evaluated immunologically. Their ability to modulate the production of cytokines was measured in vitro by their inclusion in cultures of human peripheral blood mononuclear cells (PBMC) activated by ionomycin and phorbol-12-myristate-13-acetate (PMA). The results were compared with the analogous activity of MDP. All compounds tested are strong up-regulators of IL-12 synthesis. All compounds except LK 512 also stimulated IFNgamma synthesis. LK 508, LK 511 and LK 512 are effective in up-regulating IL-2 production. LK 508 and LK 512 considerably up-regulate the synthesis of IL-4 and IL-10. LK 413 and MDP stimulated the production of Th1 promoting and Th1 (IFNgamma and IL-12) cytokines, while LK 508, LK 511 and LK 512 non-selectively up-regulated the production of both Th1 and Th2-types of (IL-4 and IL-10) cytokines. None of the phthalimido-desmuramyl dipeptides was cytotoxic in vitro against the normal cell line HUVEC (human endothelial cells) thereby indicating their potential for use in vivo.