L-alanyl-D-isoglutamine methyl ester trifluoroacetate | 88815-72-9

• 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 methyl ester trifluoroacetate
• 英文别名: methyl (4R)-5-amino-4-[[(2S)-2-aminopropanoyl]amino]-5-oxopentanoate;2,2,2-trifluoroacetic acid
• CAS: 88815-72-9
• 化学式: C₂HF₃O₂*C₉H₁₇N₃O₄
• 分子量: 345.276
• InChiKey: GQGYJAOCJNOLCF-RIHPBJNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.11
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  162
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  benzyl 2-acetamido-3-O-(D-1-carboxylethyl)-4,6-O-isopropilidene-β-D-glucopyranoside 、 L-alanyl-D-isoglutamine methyl ester trifluoroacetate 以78%的产率得到
  参考文献：
  名称：

  ISHIDA, HIDEHARU;TAKADA, KYOKO;KIGAWA, KOJI;IMAI, YASUYUKI;KISO, MAKOTO;H+, AGR. AND BIOL. CHEM., 53,(1989) N, C. 1269-1273

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (4R)-5-amino-4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]-5-oxopentanoate 、 三氟乙酸 生成 L-alanyl-D-isoglutamine methyl ester trifluoroacetate
  参考文献：
  名称：

  摘要：

  The synthesis of beta-(2-methyl-3-phenylchromonyl-7)- and beta-[2-methyl-3-(3,4-trimethylenedioxy) phenylchromonyl-7]glycosides of the methyl ester of N-acetylmuramoyl-L-alanyl-D-isoglutamine, new derivatives of a muramoyldipeptide with chromone aglycones, is described. The starting arylglycosides of N-acetylglucosamine are prepared by glycosylation of 7-hydroxychromone derivatives with the peracetate of alpha -glucosamine chloride catalyzed by a crown ether. The synthesized beta -aryl-4,6-O-isopropylidene-N-acetylmuramic acids are condensed with the dipeptide and deprotected to give the desired glycopeptides.

  DOI：

  10.1023/a:1017694224906

文献信息

• Synthesis and biological activities of N-acetyl-1-thiomuramoyl-l-alanyl-d-isoglutamine and some of its lipophilic derivatives
  作者：Akira Hasegawa、Yuichi Hioki、Makoto Kiso、Hiroyuki Okumura、Ichiro Azuma

  DOI：10.1016/0008-6215(83)88476-6

  日期：1983.11

  yl-D-isoglutamine derivatives, which were converted into the desired, lipophilic 1-thiomuramoyl dipeptides by cleavage of the isopropylidene group. Condensation of 11 with the alkyl bromides yielded the 1-S-alkyl derivatives, which were also converted, via O-deisopropylidenation and de-esterification, into the corresponding 1-S-alkylmuramoyl dipeptides. The biological activities were examined in guinea-pigs

  由苄基2-乙酰氨基-2-脱氧-4,6-O-异亚丙基-3-O- [D-1-（甲氧基羰基）合成N-乙酰基-1-硫代村酰基-L-丙氨酰基-D-异谷氨酰胺和一些亲脂性类似物）乙基]-α-D-吡喃葡萄糖苷（1）。氧化衍生自1的2，进行O-脱苯甲酰化，得到2-乙酰氨基-2-脱氧-4,6-O-异亚丙基-3-O- [D-1-（甲氧羰基）乙基] -D-吡喃葡萄糖（3） 。由四氯化碳和三（二甲基氨基）膦的作用由3形成的烷氧基-三（二甲基氨基）phosph氯化物（4）与硫代乙酸钾的缩合得到2-乙酰胺基-1-S-乙酰基-2-脱氧-4 ，6-O-异亚丙基-3-O- [D-1-（甲氧羰基）乙基] -1-硫代-β-D-吡喃葡萄糖（8）。将通过水解和随后的S-乙酰化反应从8中获得的酸9与L-丙氨酰-D-异谷氨酰胺的甲酯偶联，得到N- [2-O-（2-2-乙酰胺基-1-S-乙酰基-2] 3-二甲氧基-4，6-O-异亚丙基-
• Muramyldipeptide derivatives
  申请人：DAIICHI SEIYAKU CO., LTD.

  公开号：EP0100104A1

  公开（公告）日：1984-02-08

  Muramyldipeptide derivatives represented by the formula: wherein Ala represents alanine; Acyl represents an acyl group; R1 and R2 each represents a hydrogen atom or, when taken together, may form an alkylidene group; R3 represents a hydrogen atom, an acyl group or an alkyl group; and R4 represents a hydrogen atom or an alkyl group. These compounds have excellent immunoadjuvant activity, prophylactic and therapeutic effects against microbial infections, and antitumor activity.

  由以下式子代表的氨甲酰二肽衍生物： 其中，Ala 代表丙氨酸；Acyl 代表酰基；R1 和 R2 各代表一个氢原子，或在一起时可形成一个亚烷基；R3 代表一个氢原子、一个酰基或一个烷基；R4 代表一个氢原子或一个烷基。这些化合物具有优异的免疫佐剂活性、对微生物感染的预防和治疗作用以及抗肿瘤活性。
• Ishida, Hideharu; Kigawa, Koji; Kiso, Makoto, Agricultural and Biological Chemistry, 1991, vol. 55, # 5, p. 1343 - 1348
  作者：Ishida, Hideharu、Kigawa, Koji、Kiso, Makoto、Hasegawa, Akira、Azuma, Ichiro

  DOI：——

  日期：——
• Ishida, Hideharu; Kigawa, Koji; Imai, Yasuyuki, Agricultural and Biological Chemistry, 1989, vol. 53, # 4, p. 1057 - 1064
  作者：Ishida, Hideharu、Kigawa, Koji、Imai, Yasuyuki、Kiso, Makoto、Hasegawa, Akira、Azuma, Ichiro

  DOI：——

  日期：——
• Synthesis and biological activity of some lipophilic derivatives of 1-thio-muramoyl-l-alanyl-d-isoglutamine
  作者：Akira Hasegawa、Eiji Seki、Yuichi Hioki、Makoto Kiso、Ichiro Azuma

  DOI：10.1016/0008-6215(84)85404-x

  日期：1984.8

  2-N-Octadecanoyl derivatives of 1-S-acetyl-, 1-S-octadecanoyl-, and of 6-O-octadecanoyl-1-S-octadecanoyl-1-thiomuramoyl-L-ala nyl-D-isoglutamine were synthesized from benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-(octadecanoylamino)-beta-D-glucopy ran oside. Their immunoadjuvant activities were examined in guinea-pigs.