L-alanyl-D-isoglutamine benzyl ester hydrochloride | 59524-62-8

• 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-isoglutamine benzyl ester hydrochloride
• 英文别名: L-alanyl-D-isoglutamin-γ-benzylester hydrochloride；benzyl L-alanyl-D-isoglutaminate hydrochloride；benzyl L-alanyl-D-isoglutamine hydrochloride；H2N-L-Ala-D-iGln-OBn hydrochloride；H-L-Ala-D-Glu(OBn)-NH2*HCl；HCl*L-Ala-D-isoGln-OBn；benzyl (4R)-5-amino-4-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoate;hydrochloride
• CAS: 59524-62-8
• 化学式: C₁₅H₂₁N₃O₄*ClH
• 分子量: 343.81
• InChiKey: KKLAEFFNTIHEOR-XOZOLZJESA-N

物化性质

• 熔点：
  149-150 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  125
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  L-alanyl-D-isoglutamine benzyl ester hydrochloride 在 palladium on activated charcoal N-甲基吗啉 、 氢气 、 溶剂黄146 、 氯甲酸异丁酯 作用下， 生成 muramyl dipeptide
  参考文献：
  名称：

  Synthesis of a biologically active fluorescent muramyl dipeptide congener

  摘要：

  A fluorescent-labeled muramyl dipeptide (MDP) has been prepared to probe immunoadjuvant cellular interactions. N-Acetylmuramyl-L-alanyl-D-isoglutamine (1) was synthesized in improved yield and reacted with 2-(fluoresceinylamino)-4,6-dichloro-s-triazine (DTAF, 2) to give the fluorescent adduct DTAF-MDP (3), attached through the 6-position of the sugar moiety. Adjuvant activity was assessed by using two different in vitro assays, macrophage spreading, and inhibition of macrophage migration. Both assays indicated that the apparent adjuvant activity of 3 is comparable to that of 1.

  DOI：

  10.1021/jm00366a014
• 作为产物：
  描述：

  benzyl t-butyloxycarbonyl-L-alanyl-D-isoglutaminate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成 L-alanyl-D-isoglutamine benzyl ester hydrochloride
  参考文献：
  名称：

  Novel immunological adjuvant compounds and methods of preparation thereof

  摘要：

  该应用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分别相同或不同，为氢或酰基基团；R.sup.2为未取代或取代的烷基基团，或未取代或取代的芳基基团；X为氨基酰基基团；Y为D-异天冬酰胺或D-异谷氨酰胺。

  公开号：

  US04082735A1

文献信息

• Synthetic study of peptidoglycan partial structures. Synthesis of tetrasaccharide and octasaccharide fragments
  作者：Seiichi Inamura、Koichi Fukase、Shoichi Kusumoto

  DOI：10.1016/s0040-4039(01)01619-7

  日期：2001.10

  Partial structures of peptidoglycan, a potent immunostimulating glycoconjugate of bacteria, were synthesized for precise biological studies. A key disaccharide glucosaminyl-β(1–4)-muramic acid was prepared by stereoselective glycosylation of a N-Troc (Troc=2,2,2-trichloroethoxycarbonyl) muramic acid acceptor with a N-Troc-glucosaminyl trichloroacetimidate. The disaccharide was converted to either a

  合成了肽聚糖的部分结构，一种有效的细菌免疫刺激糖缀合物，用于精确的生物学研究。通过将N -Troc（Troc = 2,2,2-三氯乙氧基羰基）村酸受体与N -Troc-氨基葡萄糖氨基三氯乙酰胺酸酯进行立体选择性糖基化反应，制备了关键的二糖氨基葡萄糖氨基β-（1-4）-氨基乙酸。将二糖转化为二糖受体或供体。然后通过相同的糖基化方法将它们偶联在一起，以高收率得到四糖。以相似的方式也以高收率获得了八糖。ñ-乙酰化并与1-丙氨酰-d-异谷氨酰胺的二肽部分偶联，然后脱保护，首次得到了重复的肽聚糖四糖和十八肽肽缀合物。
• Synthesis of Spacered Cyclopropanoid Muramyldipeptide Analogues as Potential Immunostimulants
  作者：René Csuk、Gunnar Göthe

  DOI：10.1515/znb-2003-1216

  日期：2003.12.1

  A novel class of cyclopropanoic muramyldipeptide analogues containing an additional methylene spacer between the cyclopropane ring and the lactyl residue has been prepared by a straightforward synthesis starting from isopropyl (R)-lactate.

  一种新型的环丙酸基乙二肽类似物类别，其中在环丙烷环和乳酰残基之间含有一个额外的亚甲基间隔，已经通过从异丙基(R)-乳酸开始的简单合成制备出来。
• 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。
• ω-Aminoalkyl β-glycosides of N-acetylmuramyl-l-alanyl-d-isoglutamine, and their conjugates with meningococcal group C polysaccharide
  作者：Mitree M. Ponpipom、Kathleen M. Rupprecht

  DOI：10.1016/0008-6215(83)88218-4

  日期：1983.2

  The 6-aminohexyl beta-glycoside of N-acetylmuramyl-L-alanyl-D-isoglutamine and its spacer-arm-linked analog (3.8 nm) were synthesized from 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-alpha-D-glucopyrano)-[2,1-d]-2- oxazoline, and coupled with meningococcal group C polysaccharide in attempts to enhance the immunogenicity of the polysaccharide antigen.

  由2-甲基-（3,4,6-三-O-乙酰基）合成N-乙酰基muramyl-L-丙氨酰-D-异谷氨酰胺的6-氨基己基β-糖苷及其间隔臂连接的类似物（3.8 nm） -1,2-二脱氧-α-D-吡喃葡萄糖基）-[2,1-d] -2-恶唑啉，并与脑膜炎球菌C组多糖偶联，试图增强多糖抗原的免疫原性。
• Pig liver esterase catalyzed hydrolysis of dimethyl and diethyl 2-methyl-2-(o-nitrophenoxy)malonates
  作者：Matej Breznik、Danijel Kikelj

  DOI：10.1016/s0957-4166(96)00535-6

  日期：1997.2

  Pig liver esterase (PLE) catalyzed hydrolysis of dimethyl and diethyl 2-methyl-2-(o-nitrophenoxy)malonates affords (R)-monoethyl/monomethyl 2-methyl-2-(o-nitrophenoxy)malonates in moderate to good enantiomeric excesses (69–81 %). These data indicate that the nitro group may be accommodated in the large hydrophobic pocket of the Jones active-site model of PLE.

  猪肝酯酶（PLE）催化2-甲基-2-（邻硝基苯氧基）丙二酸二甲酯和二乙基酯的水解，得到中等至良好对映体过量的（R）-单乙基/单甲基2-甲基-2-（邻硝基苯氧基）丙二酸酯（69–81％）。这些数据表明，硝基可能被容纳在PLE的Jones活性位点模型的较大疏水口袋中。