2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-glucopyranose | 111002-40-5

• 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: 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-glucopyranose
• 英文别名: N-(2-O-<2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2,3-dideoxy-D-glucopyranos-3-yl>-(R)-lactoyl)-L-alanyl-D-isoglutamine；licopid；N-acetylglucosaminyl-N-acetylmuramyl-L-alanyl-D-isoglutamine；N-acetyl-D-glucosaminyl-β(1-4)-N-acetylmuramyl-L-alanyl-D-isoglutamine；(4R)-4-[[(2S)-2-[[(2R)-2-[(3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxypropanoyl]amino]propanoyl]amino]-5-amino-5-oxopentanoic acid
• CAS: 111002-40-5
• 化学式: C₂₇H₄₅N₅O₁₆
• 分子量: 695.678
• InChiKey: PIJXCSUPSNFXNE-AOWAGBADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.9
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  335
• 氢给体数：
  11
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  苄基(5Xi)-2-乙酰氨基-2-脱氧-4,6-O-异亚丙基-alpha-D-来苏-吡喃己糖苷 在 palladium on activated charcoal 吡啶 、 N-羟基丁二酰亚胺 、 barium hydroxide octahydrate 、 potassium tert-butylate 、 氢气 、 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 barium(II) oxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 二甲基亚砜 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 119.0h， 生成 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-glucopyranose
  参考文献：
  名称：

  细菌，细胞壁肽聚糖和某些碳水化合物类似物的重复二糖二肽单元的合成及其免疫佐剂活性。

  摘要：

  细菌细胞壁肽聚糖的重复二糖-二肽单元，其中一个是O-（N-乙酰基-β-muramoyl-L-丙氨酰-D-异谷氨酰胺）-（1导致4）-2-acetamido-2- O-（2-乙酰氨基-2-deoxy-β-D-D-葡萄糖基）-（1导致4）-N-乙酰基-村酰基-L-丙氨酰基-D-异谷氨酰胺已合成。一些碳水化合物类似物，例如O-（N-乙酰基-β-muramoyl-L-丙氨酰基-D-异谷氨酰胺）-（1导致4）-N-乙酰基-muramoyl-L-丙氨酰基-D-异谷氨酰胺，O-β-D -葡萄糖基-（1导致4）-N-乙酰基村酰基-L-丙氨酰基-D-异谷氨酰胺和O-（6-乙酰氨基-6-脱氧-β-D-葡萄糖基）-（1导致4）-N-还合成了乙酰基村酰基-L-丙氨酰基-D-异谷氨酰胺。在豚鼠中检查了它们的免疫佐剂活性。

  DOI：

  10.1016/s0008-6215(00)82587-2

文献信息

• Synthesis and Evaluation of Diverse <i>N</i> ‐Substituted Disaccharide Dipeptides for Human NOD2 Stimulation Activity
  作者：Chih‐Wei Guo、Kuo‐Ting Chen、Ting‐Yun You、Chun‐Cheng Lin、Wei‐Chieh Cheng

  DOI：10.1002/asia.202101169

  日期：2022.2.14

  The synthesis of diverse N-substituted GMDPs from an orthogonally protected disaccharide is described. The effects of both N-substituted moieties of GMDPs on the immunostimulatory activity of hNOD2 were systematically investigated.

  描述了从正交保护的二糖合成不同的 N-取代 GMDP。系统地研究了 GMDPs的两个N取代部分对 hNOD2 的免疫刺激活性的影响。
• Convenient syntheses of O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→6 and 4)-N-acetylmuramoyl-l-alanyl-d-isoglutamine
  作者：Darko Kantoci、Dina Keglević、Andrew E. Derome

  DOI：10.1016/0008-6215(89)84006-6

  日期：1989.2

  Catalytic hydrogenation of N-2-O-[benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-.beta.-D-glucopyranosyl)-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine tert-butyl ester (1) afforded N-2-O-[2-acetamido-6-O-(2-acetamido-2-deoxy-.beta.-D-glucopyranosyl)-2,3-dideoxy-D-glucopyranos-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine tert-butyl ester (2). Carboxyl-deprotection of 1 with trifluoroacetic acid gave N-2-O-[benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-.beta.-D-glucopyranosyl)-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine (3), which, on hydrogenolysis, afforded the title (1.fwdarw.6)-linked disaccharide-dipeptide 4. Coupling of benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-.beta.-D-glucopyranosyl)-6-O-benzyl-3-O-[(R)-1-carboxyethyl]-2-deoxy-.alpha.-D-glucopyranoside (6) with the benzyl ester of L-alanyl-D-isoglutamine gave N--2-O-[benzyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-.beta.-D-glucopyranosyl)-6-O-benzyl-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine benzyl ester (7). O-Deacetylation of 7 in basic media was accompanied by .alpha..fwdarw..gamma. transamidation reaction at the isoglutaminyl residue. Coupling of the O-deacetylated derivative (8) of 6 with the dipeptide benzyl ester yielded N-2-O-[benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-.beta.-D-glucopyrano-syl)-6-O-benzyl-2,3-dideoxy-.alpha.-D-glucopyranosid-3-yl]-(R)-lactoyl}-L-alanyl-D-isoglutamine benzyl ester (9) having HO-3'',4'',6'' unsubstituted. Catalytic hydrogenation of 9 afforded the title (1.fwdarw.4)-linked disaccharide-dipeptide 10.
• Synthesis and immunoadjuvant activities of the repeating, disaccharide-dipeptide unit of the bacterial, cell-wall peptidoglycan and of some carbohydrate analogs
  作者：Makoto Kiso、Yoshimi Kaneda、Reiko Shimizu、Akira Hasegawa、Ichiro Azuma

  DOI：10.1016/s0008-6215(00)82587-2

  日期：1982.6

  peptidoglycan, one being O-(N-acetyl-beta-muramoyl-L-alanyl-D-isoglutamine)-(1 leads to 4)-2-acetamido-2-deoxy-D-glucose, and the other, O-(2-acetamido-2-deoxy-beta-D-glucosyl)-(1 leads to 4)-N-acetyl-muramoyl-L-alanyl-D-isoglutamine, have been synthesized. Some carbohydrate analogs, such as O-(N-acetyl-beta-muramoyl-L-alanyl-D-isoglutamine)-(1 leads to 4)-N-acetylmuramoyl-L-alanyl-D-isoglutamine, O-beta-D-glucosyl-(1

  细菌细胞壁肽聚糖的重复二糖-二肽单元，其中一个是O-（N-乙酰基-β-muramoyl-L-丙氨酰-D-异谷氨酰胺）-（1导致4）-2-acetamido-2- O-（2-乙酰氨基-2-deoxy-β-D-D-葡萄糖基）-（1导致4）-N-乙酰基-村酰基-L-丙氨酰基-D-异谷氨酰胺已合成。一些碳水化合物类似物，例如O-（N-乙酰基-β-muramoyl-L-丙氨酰基-D-异谷氨酰胺）-（1导致4）-N-乙酰基-muramoyl-L-丙氨酰基-D-异谷氨酰胺，O-β-D -葡萄糖基-（1导致4）-N-乙酰基村酰基-L-丙氨酰基-D-异谷氨酰胺和O-（6-乙酰氨基-6-脱氧-β-D-葡萄糖基）-（1导致4）-N-还合成了乙酰基村酰基-L-丙氨酰基-D-异谷氨酰胺。在豚鼠中检查了它们的免疫佐剂活性。