Gly-Tyr-Gly | 6099-08-7

• 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: Gly-Tyr-Gly
• 英文别名: H-Gly-Tyr-Gly-OH；2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(4-hydroxyphenyl)propanoyl]amino]acetic acid
• CAS: 6099-08-7
• 化学式: C₁₃H₁₇N₃O₅
• mdl: MFCD00038181
• 分子量: 295.295
• InChiKey: HQSKKSLNLSTONK-JTQLQIEISA-N

物化性质

• 熔点：
  221 °C
• 沸点：
  753.7±60.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Gly-Tyr-Gly 在 bovine serum albumune 、 氧气 、 rose bengal 作用下， 以 水 为溶剂， 生成 [(S)-2-(2-Amino-acetylamino)-3-(1-hydroperoxy-4-oxo-cyclohexa-2,5-dienyl)-propionylamino]-acetic acid
  参考文献：
  名称：

  单线态氧介导的蛋白质氧化：在酪氨酸残基上形成反应性侧链过氧化物的证据¶

  摘要：

  摘要 单线态氧 (1O2) 由多种酶以及紫外线或可见光在敏化剂存在下产生，并已被提议作为包括白内障、晒伤和皮肤癌在内的多种病理的破坏剂。蛋白质，尤其是 Cys、Met、Trp、Tyr 和 His 侧链，由于它们的丰度和高反应速率常数，是 1O2 的主要目标。在这项研究中，表明在游离 Tyr、肽和蛋白质中的 Tyr 残基以及暴露于光化学和化学方法产生的 1O2 的模型化合物上形成长寿命过氧化物。这些物种的产量在 D2O 中显着提高，而在叠氮化物中则降低。反应混合物的核磁共振和质谱分析，或通过高效液相色谱分离的材料，与（未检测到的）内过氧化物的初始形成一致，该内过氧化物经历快速开环以产生位于 C1 环位（即酚基的对位）的氢过氧化物。在存在游离 α-氨基（例如带有游离 Tyr）的情况下，发生快速闭环，产生吲哚氢过氧化物，其衰变成相应的醇，3a-羟基-6-氧代-2,3,3a,6， 7,7a-六氢-1H-吲哚-2-羧酸。缺少游离

  DOI：

  10.1562/0031-8655(2002)076<0035:sompoe>2.0.co;2
• 作为产物：
  描述：

  N-benzyloxycarbonyl-(S)-tyrosinyl-glycine 在 甲醇 、 sodium hydroxide 、 钯 作用下， 生成 Gly-Tyr-Gly
  参考文献：
  名称：

  Abderhalden et al., Fermentforschung, 1942, vol. 16, p. 98,114

  摘要：

  DOI：

文献信息

• Tyrosinenitration affects thymidylate synthase properties
  作者：Elżbieta Dąbrowska-Maś、Tomasz Frączyk、Tomasz Ruman、Karolina Radziszewska、Piotr Wilk、Joanna Cieśla、Zbigniew Zieliński、Agata Jurkiewicz、Barbara Gołos、Patrycja Wińska、Elżbieta Wałajtys-Rode、Andrzej Leś、Joanna Nizioł、Adam Jarmuła、Piotr Stefanowicz、Zbigniew Szewczuk、Wojciech Rode

  DOI：10.1039/c1ob06360j

  日期：——

  Highly purified preparations of thymidylate synthase, isolated from calf thymus, and L1210 parental and FdUrd-resistant cells, were found to be nitrated, as indicated by a specific reaction with anti-nitro-tyrosine antibodies, suggesting this modification to appear endogenously in normal and tumor tissues. Each human, mouse and Ceanorhabditis elegans recombinant TS preparation, incubated in vitro in the presence of NaHCO3, NaNO2 and H2O2 at pH 7.5, underwent tyrosine nitration, leading to a Vmaxapp 2-fold lower following nitration of 1 (with human or C. elegans TS) or 2 (with mouse TS) tyrosine residues per monomer. Enzyme interactions with dUMP, meTHF or 5-fluoro-dUMP were not distinctly influenced. Nitration under the same conditions of model tripeptides of a general formula H2N-Gly-X-Gly-COOH (X = Phe, Tyr, Trp, Lys, Arg, His, Ser, Thr, Cys, Gly), monitored by NMR spectroscopy, showed formation of nitro-species only for H-Gly-Tyr-Gly-OH and H-Gly-Phe-Gly-OH peptides, the chemical shifts for nitrated H-Gly-Tyr-Gly-OH peptide being in a very good agreement with the strongest peak found in 15N-1H HMBC spectrum of nitrated protein. MS analysis of nitrated human and C. elegansproteins revealed several thymidylate synthase-derived peptides containing nitro-tyrosine (at positions 33, 65, 135, 213, 230, 258 and 301 in the human enzyme) and oxidized cysteine (human protein Cys210, with catalytically critical Cys195 remaining apparently unmodified) residues.

  高度纯化的胸苷酸合酶制备物，分离自小牛胸腺，以及L1210亲代细胞和FdUrd抗性细胞，被发现被硝基化，这是由与抗硝基酪氨酸抗体的特定反应所表明的，表明这种修饰在正常和肿瘤组织中内源性地出现。每个人类、小鼠和秀丽隐杆线虫的重组TS制备物，在体外pH 7.5条件下与NaHCO3、NaNO2和H2O2共孵育，经历了酪氨酸硝基化，导致每单体硝基化1（人类或秀丽隐杆线虫TS）或2（小鼠TS）个酪氨酸残基后，表观最大反应速度Vmaxapp降低2倍。酶与dUMP、meTHF或5-氟尿嘧啶-dUMP的相互作用没有明显受到影响。在相同条件下硝基化模型三肽，其一般公式为H2N-Gly-X-Gly-COOH（X = Phe, Tyr, Trp, Lys, Arg, His, Ser, Thr, Cys, Gly），通过NMR光谱监测，显示只有H-Gly-Tyr-Gly-OH和H-Gly-Phe-Gly-OH肽形成硝基物种，硝基化的H-Gly-Tyr-Gly-OH肽的化学位移与15N-1H HMBC光谱中发现的最高峰非常吻合。硝基化的人类和秀丽隐杆线虫蛋白质的MS分析揭示了几个胸苷酸合酶衍生肽，含有硝基酪氨酸（在人类酶中的位置33、65、135、213、230、258和301）和氧化半胱氨酸（人类蛋白质Cys210，具有催化关键的Cys195显然未被修饰）残基。
• 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。
• 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。