Trp-Gly-Gly | 20762-31-6

• 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: Trp-Gly-Gly
• 英文别名: WGG；H-Trp-gly-gly-OH；2-[[2-[[(2S)-2-amino-3-(1H-indol-3-yl)propanoyl]amino]acetyl]amino]acetic acid
• CAS: 20762-31-6
• 化学式: C₁₅H₁₈N₄O₄
• mdl: MFCD00037966
• 分子量: 318.332
• InChiKey: JVTHMUDOKPQBOT-NSHDSACASA-N

物化性质

• 沸点：
  787.9±60.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.266
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Trp-Gly-Gly 在 碳酸氢钠 作用下， 以 水 为溶剂， 反应 0.17h， 生成 N-Ac-L-Trp-Gly-Gly
  参考文献：
  名称：

  与细菌细胞壁粘肽前体相关的肽对125I标记的瑞斯托菌素与黄褐微球菌细胞的结合的抑制作用：定量的构效关系。

  摘要：

  已开发了N-Ac氨基酸，N-Ac二肽和N-Ac三肽在抑制125I标记的瑞氏菌素与黄褐微球菌细胞壁结合中的定量构效关系（QSAR），以探索ristocetin之间的结合细节和N-乙酰化的肽 相关方程表明（1）对于C末端氨基酸侧链具有较大摩尔折射率（MR）值的肽，其结合作用更强；（2）对于极性肽，其结合作用较弱。 （3）N-Ac二肽中的N末端氨基酸对结合亲和力的贡献是C末端氨基酸的12倍，

  DOI：

  10.1021/jm00121a018

文献信息

• Linear energy correlations and failures in the low-energy tandem mass spectra of protonatedN-benzoylated tripeptides: Tools for probing mechanisms of CAD processes
  作者：Daniel G. Morgan、Maurice M. Bursey

  DOI：10.1002/jms.1190300410

  日期：1995.4

  The backbone cleavages for three series of protonated N-benzoyl tripeptide ions were studied in a hybrid tandem mass spectrometer: (i) benzoyl-Gly-Gly-Xxx, where Xxx = Gly, Ala, Val, Leu, Ile, Phe, Tyr, Met, Glu, Pro and Trp, (ii) benzoyl-Gly-Xxx-Gly, where Xxx = Gly, Ala, Leu, Phe, Tyr, Met and Trp, and (iii) benzoyl-Xxx-Gly-Gly, where Xxx = Gly, Ala, Val, Leu, Ile, Phe, Tyr, Met, Pro and Trp. C-Terminal y-type ions and N-terminal a- and b-type ions were noted in all three cases. For benzoyl-Gly-Gly-Xxx, a linear relationship between log (y1/b2) and the proton affinity of the C-terminal amino acid substituents was found: as the proton affinity of the C-terminal residue increases, the fraction of y1 ion formation increases. A similar relationship was noted for the benzoyl-Xxx-Gly-Gly tripeptides between log (y2/b1) and the proton affinity of the N-terminal amino acid substituent: as the proton affinity of the N-terminal residue increases, the fraction of b1 ion formation increases. For the series benzoyl-Gly-Xxx-Gly, these relationships did not hold true. These observations point to similar reaction pathways throughout the benzoyl-Gly-Gly-Xxx series and also similar pathways throughout the benzoyl-Xxx-Gly-Gly, but pathways that are substituent dependent for benzoyl-Gly-Xxx-Gly. The increased correlation coefficients for benzoyl-Gly-Gly-Xxx and benzoyl-Xxx-Gly-Gly when compared with the free tripeptides, suggest that fewer interfering competitive reactions exist, as fewer possibilities for internal hydrogen bonding exist in the N-benzoyl derivatives versus the free compounds.

  在一台混合串联质谱仪上，研究了三种系列的质子化N-苯甲酰三肽离子的骨架断裂：（i）苯甲酰-Gly-Gly-Xxx，其中Xxx = Gly、Ala、Val、Leu、Ile、Phe、Tyr、Met、Glu、Pro和Trp，（ii）苯甲酰-Gly-Xxx-Gly，其中Xxx = Gly、Ala、Leu、Phe、Tyr、Met和Trp，以及（iii）苯甲酰-Xxx-Gly-Gly，其中Xxx = Gly、Ala、Val、Leu、Ile、Phe、Tyr、Met、Pro和Trp。在所有三种情况下，都观察到了C端y型离子和N端a型及b型离子。对于苯甲酰-Gly-Gly-Xxx，发现log（y1/b2）与C端氨基酸取代基的质子亲和力之间存在线性关系：随着C端残基的质子亲和力增加，y1离子的形成分数增加。对于苯甲酰-Xxx-Gly-Gly三肽，log（y2/b1）与N端氨基酸取代基的质子亲和力之间存在类似的关系：随着N端残基的质子亲和力增加，b1离子的形成分数增加。对于苯甲酰-Gly-Xxx-Gly系列，这些关系并不成立。这些观察结果表明，在苯甲酰-Gly-Gly-Xxx系列和苯甲酰-Xxx-Gly-Gly系列中存在类似的反应途径，但对于苯甲酰-Gly-Xxx-Gly，途径依赖于取代基。与自由三肽相比，苯甲酰-Gly-Gly-Xxx和苯甲酰-Xxx-Gly-Gly的相关系数增加，表明存在的干扰竞争反应较少，因为在N-苯甲酰衍生物中内部氢键的可能性比自由化合物少。
• NUTRITIVE EMULSION
  申请人：OTSUKA PHARMACEUTICAL CO., LTD.

  公开号：EP0312612A1

  公开（公告）日：1989-04-26

  The present invention provides a nutritive emulsion characterized in that the emulsion comprises essential components of about 4 to about 15% by weight of an amino acid preparation, about 3 to about 12% by weight of a lipid, about 71.5 to about 93% by weight of water, and about 0.3 to about 3.0% by weight of an emulsifier having an HLB of at least 13 and selected from the group consisting of sucrose fatty acid ester, glycerin fatty acid ester, polyoxyethylene glycerin fatty acid ester and polyoxyethylene sorbitan fatty acid ester, or an emulsifier mixture of said emulsifier and soybean lecithin and in that the emulsion has a pH of about 6.5 to about 8.5.

  本发明提供了一种营养乳剂，其特征在于该乳剂包括按重量计约4至约15%的氨基酸制剂、按重量计约3至约12%的脂质、按重量计约71.5至约93%的水、按重量计约0.3至约3.0%（重量）的乳化剂，该乳化剂的 HLB 至少为 13，并且选自由蔗糖脂肪酸酯、甘油脂肪酸酯、聚氧乙烯甘油脂肪酸酯和聚氧乙烯山梨糖醇酐脂肪酸酯组成的组，或上述乳化剂和大豆卵磷脂的乳化剂混合物，乳液的 pH 值为约 6.5 至约 8.5。
• C-TERMINUS AMIDATION ENZYME COMPOSITION, PROCESS FOR ITS PREPARATION AND ITS USE
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP0447547A1

  公开（公告）日：1991-09-25

  A C-terminus amidation enzyme composition of serum or blood plasma origin, which acts on a C-terminus glycine adduct represented by formula (I) (wherein A represents a residue other than α-amino or imino group and α-carboxyl group of a natural α-amino acid origin, and X represents a hydrogen atom or a residue of an amino acid derivative bound to the N atom via a carbonyl group) to produce a C-terminus amidation product represented by formula (II) (wherein A and X are as defined above) and glyoxylic acid, is disclosed. A process for preparing the composition and its use are also disclosed.

  一种来源于血清或血浆的 C-端酰胺化酶组合物，它作用于式(I)代表的 C-端甘氨酸加合物（其中 A 代表除天然 α-氨基酸来源的 α-氨基或亚胺基和 α-羧基以外的残基），X 代表氢原子或通过羰基与 N 原子结合的氨基酸衍生物残基、和 X 代表氢原子或通过羰基与 N 原子结合的氨基酸衍生物残基），以产生由式 (II) 代表的 C 端酰胺化产物（其中 A 和 X 如上定义）和乙醛酸。还公开了制备该组合物的工艺及其用途。
• Enzyme participating in c-terminal amidation, and method of preparing same and use thereof
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP0666318A1

  公开（公告）日：1995-08-09

  An enzyme catalyzing the conversion of a peptide C-terminal glycine adduct represented by the following formula (I): (wherein A represents a residue other than α-amino group or imino group and α-carboxylic group derived from naturally occurring α-amino acid, X represents hydrogen atom or a residue of an amino acid derivative which is bonded to N atom through carbonyl group) to a peptide C-terminal α-hydroxyglycine adduct represented by the following formula (II): (wherein A and X have the same meanings as above), and further catalyzing the conversion of the peptide C-terminal α-hydroxylglycine adduct represented by the above formula (II) to a C-terminal amidated compound represented by the following formula (III): (wherein A and X have the see meanings as defined above), which comprises culturing host cells transformed with an expression plasmid comprising a DNA coding for said enzyme, and recovering both or either of said enzymes from the culture, characterized in that in said DNA a portion corresponding to the membrane spanning region has been excised.

  催化下式（I）所代表的肽 C 端甘氨酸加合物转化的酶： (其中 A 代表α-氨基或亚胺基和α-羧基以外的残基，α-氨基或亚胺基和α-羧基来自天然存在的α-氨基酸，X 代表氢原子或通过羰基与 N 原子结合的氨基酸衍生物残基)转化为下式(II)代表的肽 C-末端α-羟基甘氨酸加合物： (其中A和X的含义同上)，并进一步催化由上式(II)代表的肽C-末端α-羟基甘氨酸加合物转化为由下式(III)代表的C-末端酰胺化化合物： (其中A和X的含义与上式相同)，其中包括培养用包含编码上述酶的DNA的表达质粒转化的宿主细胞，并从培养物中回收上述两种或其中一种酶，其特征在于，在上述DNA中，对应于跨膜区的部分已被切除。
• Enzyme participating in C-terminal amidation, and method of preparing same and use thereof
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP0884389A1

  公开（公告）日：1998-12-16

  An enzyme participating in C-terminal amidation which acts on a peptide C-terminal glycine adduct represented by the following formula (I): (wherein A represents a residue other than α-amino group or imino group and α-carboxylic group derived from naturally occurring α-amino acid, X represents hydrogen atom or a residue of an amino acid derivative which is bonded to N atom through carbonyl group) to form a peptide C-terminal α-hydroxylglycine adduct represented by the following formula (II): (wherein A and X have the same meanings as above, and an enzyme participating in peptide C-terminal amidation of a peptide terminal glycine adduct which acts on a peptide C-terminal α-hydroxylglycine adduct represented by the above formula (II) to form a C-terminal amidated compound represented by the following formula (III): (wherein A and X have the same meanings as described above) a method of producing the same, and the use thereof.

  一种参与 C 端酰胺化的酶，它作用于由下式（I）代表的肽 C 端甘氨酸加合物： (其中 A 代表α-氨基或亚胺基和α-羧基以外的残基，X 代表氢原子或通过羰基与 N 原子结合的氨基酸衍生物残基），以形成下式（II）所代表的肽 C-末端α-羟基甘氨酸加合物： (其中 A 和 X 的含义同上，以及一种参与肽 C-末端甘氨酸加合物酰胺化的酶，该酶作用于上式(II)代表的肽 C-末端α-羟基甘氨酸加合物，形成下式(III)代表的 C-末端酰胺化化合物： (其中A和X的含义与上述相同）的生产方法及其用途。

表征谱图