N-acetylglutaminylglutamine | 69624-04-0

• 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: N-acetylglutaminylglutamine
• 英文别名: NAGG；(2S)-2-[[(2S)-2-acetamido-5-amino-5-oxopentanoyl]amino]-5-amino-5-oxopentanoic acid
• CAS: 69624-04-0
• 化学式: C₁₂H₂₀N₄O₆
• 分子量: 316.314
• InChiKey: KKQQDQHEOLWKFV-YUMQZZPRSA-N

物化性质

• 沸点：
  914.4±65.0 °C(Predicted)
• 密度：
  1.343±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 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：
  182
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-acetylglutaminylglutamine 在 Sinorhizobium meliloti AsnO gene 作用下， 生成 (2S)-2-乙酰氨基-N-[(2S)-1,5-二氨基-1,5-二氧代戊烷-2-基]戊烷二酰胺
  参考文献：
  名称：

  Osmotically induced synthesis of the dipeptide N-acetylglutaminylglutamine amide is mediated by a new pathway conserved among bacteria

  摘要：

  二肽N-乙酰谷氨酰谷氨酰胺（NAGGN）最初在高渗压下培养的Sinorhizobium meliloti细菌中被发现，并随后被证明由一些渗透压挑战的细菌合成和积累。然而，其生物合成途径仍然未知。最近，在Pseudomonas aeruginosa中发现了两个基因，这些基因可能编码谷氨酰胺转移酶和乙酰转移酶，并受渗透压的上调作用。在这项工作中，鉴定了携带S. meliloti中同源基因的基因座，asnO和ngg，并报道了NAGGN生物合成途径的遗传和分子特征。通过使用NMR实验，发现失活于asnO和ngg的菌株无法产生二肽。这种无能力对S. meliloti在高渗压下的生长具有有害影响，证明了NAGGN生物合成在细胞渗透保护中的关键作用。转录融合的β-葡萄糖醛酸酶活性显示，在增加的NaCl浓度下生长的细胞中，asnO表达被强烈诱导，与NAGGN的积累相一致。 asnO - ngg簇编码一种介导非核糖肽合成的独特酶机。该途径首先涉及Ngg，一种催化中间体N-乙酰谷氨酰谷氨酰胺形成的双功能酶，其次是AsnO，需要进行后续酰胺基的添加和将N-乙酰谷氨酰谷氨酰胺转化为NAGGN。有趣的是，在许多具有不同生活方式的细菌中观察到asnO - ngg簇的强烈保守性，如海洋、共生和致病细菌，突显了NAGGN合成能力在渗透保护和细菌宿主细胞相互作用中的生态重要性。

  DOI：

  10.1073/pnas.1003063107
• 作为产物：
  描述：

  L-谷氨酰胺 、 乙酰辅酶A 在 Sinorhizobium meliloti Ngg gene 作用下， 生成 N-acetylglutaminylglutamine
  参考文献：
  名称：

  Osmotically induced synthesis of the dipeptide N-acetylglutaminylglutamine amide is mediated by a new pathway conserved among bacteria

  摘要：

  二肽N-乙酰谷氨酰谷氨酰胺（NAGGN）最初在高渗压下培养的Sinorhizobium meliloti细菌中被发现，并随后被证明由一些渗透压挑战的细菌合成和积累。然而，其生物合成途径仍然未知。最近，在Pseudomonas aeruginosa中发现了两个基因，这些基因可能编码谷氨酰胺转移酶和乙酰转移酶，并受渗透压的上调作用。在这项工作中，鉴定了携带S. meliloti中同源基因的基因座，asnO和ngg，并报道了NAGGN生物合成途径的遗传和分子特征。通过使用NMR实验，发现失活于asnO和ngg的菌株无法产生二肽。这种无能力对S. meliloti在高渗压下的生长具有有害影响，证明了NAGGN生物合成在细胞渗透保护中的关键作用。转录融合的β-葡萄糖醛酸酶活性显示，在增加的NaCl浓度下生长的细胞中，asnO表达被强烈诱导，与NAGGN的积累相一致。 asnO - ngg簇编码一种介导非核糖肽合成的独特酶机。该途径首先涉及Ngg，一种催化中间体N-乙酰谷氨酰谷氨酰胺形成的双功能酶，其次是AsnO，需要进行后续酰胺基的添加和将N-乙酰谷氨酰谷氨酰胺转化为NAGGN。有趣的是，在许多具有不同生活方式的细菌中观察到asnO - ngg簇的强烈保守性，如海洋、共生和致病细菌，突显了NAGGN合成能力在渗透保护和细菌宿主细胞相互作用中的生态重要性。

  DOI：

  10.1073/pnas.1003063107

文献信息

• Osmoprotective Complexes for Prevention of Intra-cellular Dehydration in Mammals
  申请人：GUPTA SHYAM K.

  公开号：US20110124573A1

  公开（公告）日：2011-05-26

  This invention relates to certain Aloesin derivatives with natural amino acids, peptides, and amino sugars (formula I). The compounds of the present invention possess osmoprotective properties, which are suitable for topical or oral application to treat dermatological disorders including challenged skin 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：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