D-丙氨酸-L-谷氨酰胺 | 205252-36-4

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 谷氨酰胺类衍生物
• 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
• 中文名称: D-丙氨酸-L-谷氨酰胺
• 中文别名: D-丙氨酰-L-谷氨酰胺
• 英文名称: D-Ala-L-Gln
• 英文别名: D-Alanyl-L-glutamine；(2S)-5-amino-2-[[(2R)-2-aminopropanoyl]amino]-5-oxopentanoic acid
• CAS: 205252-36-4
• 化学式: C₈H₁₅N₃O₄
• 分子量: 217.225
• InChiKey: HJCMDXDYPOUFDY-UHNVWZDZSA-N

物化性质

• 沸点：
  615.4±55.0 °C(Predicted)
• 密度：
  1.305±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  136
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  D-丙氨酸-L-谷氨酰胺 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.25h， 生成 Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-[(S)-2-((R)-2-benzyloxycarbonylamino-propionylamino)-4-carbamoyl-butyrylamino]-6-methyl-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis and Activity of Dipeptides, Linked to Targeting Ligands, as Specific NK Cell Enhancers

  摘要：

  Water soluble analogues of the lipophilic immunostimulant, octadecyl D-alanyl-L-glutamine, BCH-527, were synthesized and evaluated for the ability to stimulate natural killer (NK) cells. One of these compounds in which the octadecyl chain of BCH-527 was replaced with a shorter chain alcohol, 6-(D-alanyl-L-glutaminylamino)hexan-1-ol, 9, displayed an in vitro stimulation of NK cells comparable to that of interleukin 2 (IL 2). However, when the hydroxyl of 9 was linked to L-fucose to yield 1-beta-[6-(D-alanyl-L-glutaminylamino)hex-1-yl]-L-fucopyranose (BCH-2537 1), the observed stimulation of NK cells was greater than that observed with IL 2. Further evaluation of these compounds revealed that the improved in vitro activity of BCH-2537 was more pronounced in vivo. That is, while both compounds significantly increased splenic NK cells, only BCH-2537 significantly increased the activity of these cells in vivo. In terms of a structure-activity relationship, NK cell activity was sensitive to minor structural modifications. It was influenced by conservative substitutions within the dipeptide, the length of the hydrocarbon chain, and the functionality at the end of the chain. No other compound enhanced NK cell activity to the extent exhibited by BCH-2537, although a few were equipotent to 9.

  DOI：

  10.1021/jm970734v

文献信息

• ALANYL GLUTAMINE COMPOUND AND PREPARATION METHOD THEREOF
  申请人：Tao Linggang

  公开号：US20150038740A1

  公开（公告）日：2015-02-05

  A process for preparing a pure alanylglutamine comprises the steps of: 1) reacting N-(α-chloro)-propionyl-glutamine and hydrazine compound to obtain an alanylglutamine crude product; 2) mixing anhydrous methanol and the alanylglutamine crude product to provide a filter cake; 3) dissolving the filter cake in water, heating, adding ethanol, and cooling to yield the pure alanylglutamine.

  制备纯丙氨酰谷氨酰胺的过程包括以下步骤：1）将N-(α-氯代)-丙酰谷氨酰胺与肼化合物反应，得到丙氨酰谷氨酰胺粗品；2）混合无水甲醇和丙氨酰谷氨酰胺粗品以提供过滤蛋糕；3）将过滤蛋糕溶解在水中，加热，加入乙醇，冷却以得到纯丙氨酰谷氨酰胺。
• DIPEPTIDE CRYSTALS AND PROCESS FOR PRODUCTION THEREOF
  申请人：KYOWA HAKKO KOGYO CO., LTD.

  公开号：EP1870457A1

  公开（公告）日：2007-12-26

  The present invention provides: (1) crystals of a dipeptide which do not substantially comprise a dipeptide comprising D-amino acid as a constituent or a polypeptide consisting of three or more amino acids; and (2) crystals of a dipeptide which do not substantially comprise a dipeptide comprising D-amino acid as a constituent, a polypeptide consisting of three or more amino acids, or an amino acid amide; and a process for producing the dipeptide crystals.

  本发明提供了：(1) 一种二肽的晶体，该晶体实质上不包括以 D-氨基酸为成分的二肽或由三个或三个以上氨基酸组成的多肽；(2) 一种二肽的晶体，该晶体实质上不包括以 D-氨基酸为成分的二肽、由三个或三个以上氨基酸组成的多肽或氨基酸酰胺；以及一种生产二肽晶体的工艺。
• NOVEL LIPOPHILIC OLIGOPEPTIDES WITH IMMUNOMODULATING ACTIVITY
  申请人：BIOCHEM PHARMA INC.

  公开号：EP0635026B1

  公开（公告）日：1999-11-10
• US9024064B2
  申请人：——

  公开号：US9024064B2

  公开（公告）日：2015-05-05
• Synthesis and Activity of Dipeptides, Linked to Targeting Ligands, as Specific NK Cell Enhancers
  作者：Shaun D. Abbott、Lyne Gagnon、Mouna Lagraoui、Salam Kadhim、Giorgio Attardo、Boulos Zacharie、Christopher L. Penney

  DOI：10.1021/jm970734v

  日期：1998.5.1

  Water soluble analogues of the lipophilic immunostimulant, octadecyl D-alanyl-L-glutamine, BCH-527, were synthesized and evaluated for the ability to stimulate natural killer (NK) cells. One of these compounds in which the octadecyl chain of BCH-527 was replaced with a shorter chain alcohol, 6-(D-alanyl-L-glutaminylamino)hexan-1-ol, 9, displayed an in vitro stimulation of NK cells comparable to that of interleukin 2 (IL 2). However, when the hydroxyl of 9 was linked to L-fucose to yield 1-beta-[6-(D-alanyl-L-glutaminylamino)hex-1-yl]-L-fucopyranose (BCH-2537 1), the observed stimulation of NK cells was greater than that observed with IL 2. Further evaluation of these compounds revealed that the improved in vitro activity of BCH-2537 was more pronounced in vivo. That is, while both compounds significantly increased splenic NK cells, only BCH-2537 significantly increased the activity of these cells in vivo. In terms of a structure-activity relationship, NK cell activity was sensitive to minor structural modifications. It was influenced by conservative substitutions within the dipeptide, the length of the hydrocarbon chain, and the functionality at the end of the chain. No other compound enhanced NK cell activity to the extent exhibited by BCH-2537, although a few were equipotent to 9.