Ac-Glu-Glu-OH | 28809-18-9

• 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: Ac-Glu-Glu-OH
• 英文别名: 2-(2-Acetylamino-4-carboxy-butyrylamino)-pentanedioic acid；(2S)-2-[[(2S)-2-acetamido-4-carboxybutanoyl]amino]pentanedioic acid
• CAS: 28809-18-9
• 化学式: C₁₂H₁₈N₂O₈
• 分子量: 318.284
• InChiKey: OLBUBQCXGZCOQZ-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  170
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  H-Glu(OBzl)-Glu(OBzl)-OBzl 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 4.0~25.0 ℃ 、275.79 kPa 条件下， 反应 6.0h， 生成 Ac-Glu-Glu-OH
  参考文献：
  名称：

  Synthesis of acyclic and dehydroaspartic acid analogs of Ac-Asp-Glu-OH and their inhibition of rat brain N-acetylated .alpha.-linked acidic dipeptidase (NAALA dipeptidase)

  摘要：

  The following structural and conformationally constrained analogues of Ac-Asp-Glu-OH (1) were synthesized: Ac-Glu-Glu-OH (2), Ac-D-Asp-Glu-OH (3), Ac-Glu-Asp-OH (4), Ac-Asp-Asp-OH (5), Ac-Asp-3-aminohexanedioic acid (6), Ac-3-amino-3-(carboxymethyl)propanoyl-Glu-OH (7), N-succinyl-Glu-OH (8), N-maleyl-Glu-OH (9), N-fumaryl-Glu-OH (10), and Ac-delta ZAsp-Glu-OH (11). These analogues were evaluated for their ability to inhibit the hydrolysis of Ac-Asp-[3,4-3H]-Glu-OH by N-acetylated alpha-linked acidic dipeptidase (NAALA dipeptidase) in order to gain some insight into the structural requirements for the inhibition of this enzyme. Analogues 4-6 and 9 were very weak inhibitors of NAALA dipeptidase (Ki greater than 40 microM), while 2, 3, and 7 with Ki values ranging from 3.2-8.5 microM showed intermediate inhibitory activity. The most active inhibitors of NAALA dipeptidase were compounds 8, 10, and 11 with Ki values of 0.9, 0.4, and 1.4 microM, respectively. These results suggest that the relative spacing between the side chain carboxyl and the alpha-carboxyl group of the C-terminal residue may be important for binding to the active site of the enzyme. They also indicate that the chi 1 torsional angle for the aspartyl residue is in the vicinity of 0 degrees.

  DOI：

  10.1021/jm00172a009

文献信息

• SUBASINGHE, NALIN;SCHULTE, MARVIN;CHAN, MICHAEL Y. -M.;ROON, ROBERT J.;KO+, J. MED. CHEM., 33,(1990) N0, C. 2734-2744
  作者：SUBASINGHE, NALIN、SCHULTE, MARVIN、CHAN, MICHAEL Y. -M.、ROON, ROBERT J.、KO+

  DOI：——

  日期：——
• Prevention of Cellular Senescence in Mammals by Natural Peptide Complexes
  申请人：GUPTA SHYAM K.

  公开号：US20110190202A1

  公开（公告）日：2011-08-04

  Preventing skin aging by targeting multiple causes by a single bullet is of primal scientific and consumer interest. A treatment based on compositions of compound (I) for cellular senescence to control cellular degradation offers such a solution to multiple skin ailments including skin degradation from cancer, diabetes, radiation treatments, chemotherapy, and sun-burn; mitochondrial dysfunction, age spots, acne, loss of cellular antioxidants, collagen loss, loss of skin pliability, loss of skin suppleness, skin wrinkles including fine lines, oxidation, damage from radiation, damage from free radicals, damage from UV, dry skin, xerosis, ichthyosis, dandruff, brownish spots, keratoses, melasma, lentigines, liver spots, pigmented spots, dark circles under the eyes, skin pigmentation including darkened skin, blemishes, oily skin, warts, eczema, pruritic skin, psoriasis, inflammatory dermatoses, topical inflammation, disturbed keratinization, skin changes associated with aging, scalp dryness, skin depigmentation, intracellular dehydration, and combinations thereof;
• PREVENTION OF CELLULAR SENESCENCE IN MAMMALS BY NATURAL PEPTIDE COMPLEXES
  申请人：Gupta Shyam K.

  公开号：US20120264696A1

  公开（公告）日：2012-10-18

  Preventing skin aging by targeting multiple causes by a single bullet is of primal scientific and consumer interest. A treatment based on compositions of compound (I) for cellular senescence to control cellular degradation offers such a solution to multiple skin ailments including skin degradation from cancer, diabetes, radiation treatments, chemotherapy, and sun-burn; mitochondrial dysfunction, age spots, acne, loss of cellular antioxidants, collagen loss, loss of skin pliability, loss of skin suppleness, skin wrinkles including fine lines, oxidation, damage from radiation, damage from free radicals, damage from UV, dry skin, xerosis, ichthyosis, dandruff, brownish spots, keratoses, melasma, lentigines, liver spots, pigmented spots, dark circles under the eyes, skin pigmentation including darkened skin, blemishes, oily skin, warts, eczema, pruritic skin, psoriasis, inflammatory dermatoses, topical inflammation, disturbed keratinization, skin changes associated with aging, scalp dryness, skin depigmentation, intracellular dehydration, and combinations thereof;
• US8212076B2
  申请人：——

  公开号：US8212076B2

  公开（公告）日：2012-07-03
• US8258343B1
  申请人：——

  公开号：US8258343B1

  公开（公告）日：2012-09-04