3-(羟甲基)-L-酪氨酸 | 41679-15-6

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 酪氨酸类衍生物
• 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: 3-(羟甲基)-L-酪氨酸
• 英文名称: (S)-4-hydroxy-3-hydroxymethylphenylalanine
• 英文别名: L-3-hydroxymethyltyrosine；L-3-Hydroxymethyltyrosin；(2S)-2-azaniumyl-3-[4-hydroxy-3-(hydroxymethyl)phenyl]propanoate
• CAS: 41679-15-6
• 化学式: C₁₀H₁₃NO₄
• 分子量: 211.218
• InChiKey: RDBXZNZJKNWRCZ-QMMMGPOBSA-N

物化性质

• 熔点：
  >300℃
• 沸点：
  424.6±33.0 °C(Predicted)
• 密度：
  1.411

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(羟甲基)-L-酪氨酸 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 sodium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 生成 (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[4-hydroxy-3-(hydroxymethyl)phenyl]propanoic acid
  参考文献：
  名称：

  Tyrosine analogues as alternative substrates for protein tyrosine kinase Csk: Insights into substrate selectivity and catalytic mechanism

  摘要：

  Protein tyrosine kinases are critical enzymes in cell signal transduction but relatively little is known about the molecular recognition of the tyrosine substrate by these enzymes. Details of tyrosine substrate specificity within the context of a short peptide were investigated for protein tyrosine kinase Csk. It was found that aryl ring functional group substitutions the size of methyl group or smaller were generally well tolerated by the protein tyrosine kinase Csk whereas larger groups caused a decline in substrate efficiency. Extension of the phenol from the peptide backbone by a single methylene was acceptable for phosphorylation whereas removal of a methylene nearly abolished reactivity. Only the L-tyrosine derivative was processed. A negative charge ortho to the phenol hydroxyl was incompatible with substrate reactivity, consistent with previous pH rate profiles which indicated the importance of the neutral phenol. Overall, these studies confirmed the interpretation of a previous linear free energy relationship analysis which suggested that the enzyme followed a dissociative transition state mechanism. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00053-5
• 作为产物：
  描述：

  N-苄氧羰基-L-酪氨酸 在 三氯化硼 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 5.17h， 生成 3-(羟甲基)-L-酪氨酸
  参考文献：
  名称：

  A convenient two step transformation of tyrosine into the antihypertensive amino acid (S)-4-hydroxy-3-hydroxymethylphenylalanine

  摘要：

  Treatment of tyrosine with paraformaldehyde and catalytic amounts of p-toluenesulfonic acid, at reflux in toluene, directly generates benzyl (S)-4-(4H-1,3-benzodioxin-6-ylmethyl)-5-oxo-1,3-oxazolane-3-carboxylate, which on treatment with boron trichloride in dichloromethane, affords (S)-4-hydroxy-3-hydroxymethylphenylalanine. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2004.02.031

文献信息

• PROBE COMPOUNDS FOR PROTEIN TYROSINE PHOSPHATASE (PTP) AND PRECURSORS THEREOF
  申请人：Lo Lee-Chiang

  公开号：US20100317831A1

  公开（公告）日：2010-12-16

  A probe compound for protein tyrosine phosphatases (PTPs), as shown in Formula (I) is provided. In Formula (I), A 1 and A 2 represent amino acids. The amino acids include leucine, phenylalanine, glutamic acid, lysine, alanine, arginine, aspartic acid, asparagine, citrulline, cysteine, cystine, glutamine, glycine, histidine, hydroxyproline, isoleucine, methionine, proline, serine, threonine, tryptophan, valine or a combination thereof. The invention also provides probe compound precursors for protein tyrosine phosphatases (PTPs).

  提供了一种用于蛋白酪氨酸磷酸酶（PTPs）的探针化合物，如式（I）所示。在式（I）中，A1和A2代表氨基酸。这些氨基酸包括亮氨酸、苯丙氨酸、谷氨酸、赖氨酸、丙氨酸、精氨酸、天冬氨酸、天冬酰胺、瓜氨酸、半胱氨酸、胱氨酸、谷氨酰胺、甘氨酸、组氨酸、羟脯氨酸、异亮氨酸、蛋氨酸、脯氨酸、丝氨酸、苏氨酸、色氨酸、缬氨酸或其组合。该发明还提供了用于蛋白酪氨酸磷酸酶（PTPs）的探针化合物前体。
• Lyase Enzymes, Nucleic Acids Encoding Them and Methods for Making and Using Them
  申请人：Weiner David

  公开号：US20110027346A1

  公开（公告）日：2011-02-03

  This invention provides polypeptides having lyase activity, polynucleotides encoding these polypeptides, and methods of making and using these polynucleotides and polypeptides. In one aspect, the invention is directed to polypeptides having ammonia lyase activity, e.g., phenylalanine ammonia lyase, tyrosine ammonia lyase and/or histidine ammonia lyase activity, including thermostable and thermotolerant activity, and polynucleotides encoding these enzymes, and making and using these polynucleotides and polypeptides. The polypeptides of the invention can be used in a variety of pharmaceutical, agricultural and industrial contexts.

  这项发明提供了具有裂解酶活性的多肽，编码这些多肽的多核苷酸以及制备和使用这些多核苷酸和多肽的方法。在一个方面，该发明涉及具有氨裂解酶活性的多肽，例如苯丙氨酸裂解酶、酪氨酸裂解酶和/或组氨酸裂解酶活性，包括热稳定和耐热活性，以及编码这些酶的多核苷酸，以及制备和使用这些多核苷酸和多肽。该发明的多肽可用于各种制药、农业和工业领域。
• L-3-hydroxymethyltyrosine and salts thereof for lowering blood pressure
  申请人：Richardson-Merrell Inc.

  公开号：US04022910A1

  公开（公告）日：1977-05-10

  L-3-Hydroxymethyltyrosine and pharmaceutically acceptable salts thereof useful in lowering blood pressure and compositions thereof.

  L-3-羟甲基酪氨酸及其药用盐在降低血压和其组合物中有用。
• Synthesis of hydantoin containing peptide products
  申请人：SANOFI-AVENTIS DEUTSCHLAND GMBH

  公开号：US10087221B2

  公开（公告）日：2018-10-02

  The present invention relates to a method of synthesizing a peptide product comprising at least one hydantoin group. The peptide product may be used as a reference material for the quality control of pharmaceutical peptides, particularly for the quality control of exendin peptides. Further, the invention relates to hydantoin building blocks, a method for manufacturing such building blocks and their use for the synthesis of peptide products.

  本发明涉及一种合成包含至少一个海因基团的多肽产品的方法。该多肽产品可用作药物多肽质量控制的参考材料，特别是用于外激素多肽的质量控制。此外，本发明还涉及海因砌块、制造这种砌块的方法及其用于合成肽产品的用途。
• LYASE ENZYMES, NUCLEIC ACIDS ENCODING THEM AND METHODS FOR MAKING AND USING THEM
  申请人：BASF Enzymes LLC

  公开号：EP1869174B1

  公开（公告）日：2015-02-18