N-boc-4-hydroxymethylphenylalanine | 160916-46-1

• 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-boc-4-hydroxymethylphenylalanine
• 英文别名: BocTyr(CH2OH)OH；(2S)-3-[4-(hydroxymethyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 160916-46-1
• 化学式: C₁₅H₂₁NO₅
• 分子量: 295.335
• InChiKey: CLRXKBZFTMLYOD-LBPRGKRZSA-N

物化性质

• 沸点：
  497.3±45.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-boc-4-hydroxymethylphenylalanine 在 吡啶 、 potassium permanganate 、 戴斯-马丁氧化剂 、 sodium hydroxide 作用下， 以 乙醚 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 0.3h， 生成 N-Boc-4-羧基苯丙氨酸甲酯
  参考文献：
  名称：

  COMPOSITIONS CONTAINING, METHODS INVOLVING, AND USES OF NON-NATURAL AMINO ACIDS AND POLYPEPTIDES

  摘要：

  公开号：

  EP1828224B1
• 作为产物：
  描述：

  N-Boc-4-羧基苯丙氨酸甲酯 在 lithium hydroxide 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 N-boc-4-hydroxymethylphenylalanine
  参考文献：
  名称：

  环状氨基六肽的全合成和抗真菌评估。

  摘要：

  对治疗全身性真菌感染的新疗法的需求持续增长。天然存在的六肽棘皮菌素B（1）通过抑制β-1,3葡聚糖（一种重要的真菌细胞壁成分）的合成，显示出强大的抗真菌活性。尽管到目前为止，由于该试剂的理化特性而受到限制，但我们发现在“西北”位置带有氨基脯氨酸残基的类似物的合成可大大改善水溶性（> 5 mg / mL）。报道了基于整个细胞和一系列化合物的体内活性的合成和构效关系（SAR）。

  DOI：

  10.1016/s0968-0896(00)00097-3

文献信息

• Synthesis of novel chiral amino acids possessing a porphyrin moiety
  作者：Hitoshi Tamiaki、Motoki Onishi

  DOI：10.1016/s0957-4166(99)00101-9

  日期：1999.3

  Phenylalanine derivatives bearing a porphyrin moiety at the para-position were prepared in an enantiomerically pure form. The synthetic nonnatural aromatic amino acid reacted with amines and acids to give novel functionalized peptides without loss of the enantiomeric purity.

  以对映体纯的形式制备在对位带有卟啉部分的苯丙氨酸衍生物。合成的非天然芳族氨基酸与胺和酸反应，得到新的功能化肽，而不会损失对映体纯度。
• Compositions Containing, Methods Involving, and Uses of Non-Natural Amino Acids and Polypeptides
  申请人：Miao Zhenwei

  公开号：US20090240029A1

  公开（公告）日：2009-09-24

  Disclosed herein are non-natural amino acids and polypeptides that include at least one non-natural amino acid, and methods for making such non-natural amino acids and polypeptides. The non-natural amino acids, by themselves or as a part of a polypeptide, can include a wide range of possible functionalities, but typical have at least one heterocycle, aldol-based, dicarbonyl, and/or diamine group. Also disclosed herein are non-natural amino acid polypeptides that are further modified post-translationally, methods for effecting such modifications, and methods for purifying such polypeptides. Typically, the modified non-natural amino acid polypeptides include at least one heterocycle, aldol-based, dicarbonyl, and/or diamine group. Further disclosed are methods for using such non-natural amino acid polypeptides and modified non-natural amino acid polypeptides, including therapeutic, diagnostic, and other biotechnology uses.

  本文披露了非天然氨基酸和多肽，其中包括至少一个非天然氨基酸，以及制备这种非天然氨基酸和多肽的方法。这些非天然氨基酸本身或作为多肽的一部分，可以包括各种可能的功能，但通常至少具有一个杂环，醛缩基，二羰基和/或二胺基团。本文还披露了经翻译后进一步修饰的非天然氨基酸多肽，以及实现这种修饰的方法和纯化这种多肽的方法。通常，修饰后的非天然氨基酸多肽包括至少一个杂环，醛缩基，二羰基和/或二胺基团。此外，还披露了使用这种非天然氨基酸多肽和经修饰的非天然氨基酸多肽的方法，包括治疗，诊断和其他生物技术用途。
• Compositions containing, methods involving, and uses of non-natural amino acids and polypeptides
  申请人：Ambrx, Inc.

  公开号：EP2399893A2

  公开（公告）日：2011-12-28

  Disclosed herein are non-natural amino acids and polypeptides that include at least one non-natural amino acid, and methods for making such non-natural amino acids and polypeptides. The non-natural amino acids, by themselves or as a part of a polypeptide, can include a wide range of possible functionalities, but typical have at least one oxime, carbonyl, dicarbonyl, and/or hydroxylamine group. Also disclosed herein are non-natural amino acid polypeptides that are further modified post-translationally, methods for effecting such modifications, and methods for purifying such polypeptides. Typically, the modified non-natural amino acid polypeptides include at least one oximine, carbonyl, dicarbonyl, and/or hydroxylamine group. Further disclosed are methods for using such non-natural amino acid polypeptides and modified non-natural amino acid polypeptides, including therapeutic, diagnostic, and other biotechnology uses.

  本文公开了非天然氨基酸和包括至少一种非天然氨基酸的多肽，以及制造这种非天然氨基酸和多肽的方法。非天然氨基酸本身或作为多肽的一部分，可包括多种可能的官能团，但典型的至少有一个肟基、羰基、二羰基和/或羟胺基。本文还公开了经翻译后进一步修饰的非天然氨基酸多肽、进行此类修饰的方法以及纯化此类多肽的方法。通常，修饰的非天然氨基酸多肽包括至少一个肟基、羰基、二羰基和/或羟胺基团。进一步公开的是使用这种非天然氨基酸多肽和修饰的非天然氨基酸多肽的方法，包括治疗、诊断和其它生物技术用途。
• Structure-Based Design, Synthesis, and Biological Evaluation of Irreversible Human Rhinovirus 3C Protease Inhibitors. 2. Peptide Structure−Activity Studies
  作者：Peter S. Dragovich、Stephen E. Webber、Robert E. Babine、Shella A. Fuhrman、Amy K. Patick、David A. Matthews、Siegfried H. Reich、Joseph T. Marakovits、Thomas J. Prins、Ru Zhou、Jayashree Tikhe、Ethel S. Littlefield、Ted M. Bleckman、Michael B. Wallace、Thomas L. Little、Clifford E. Ford、James W. Meador、Rose Ann Ferre、Edward L. Brown、Susan L. Binford、Dorothy M. DeLisle、Stephen T. Worland

  DOI：10.1021/jm9800696

  日期：1998.7.1

  The structure-based design, chemical synthesis, and biological evaluation of various peptide-derived human rhinovirus (HRV) 3C protease (3CP) inhibitors are described. These compounds are comprised of an ethyl propenoate Michael acceptor moiety and a tripeptidyl binding determinant. The systematic modification of each amino acid residue present in the binding determinant as well as the N-terminal functionality is described. Such modifications are shown to provide irreversible HRV-14 3CP inhibitors with anti-3CP activities (k(obs)/[I]) ranging from 60 to 280 000 M-1 s(-1) and antiviral EC50's which approach 0.15 mu M. An optimized inhibitor which incorporates several improvements identified by the structure-activity studies is also described. This molecule displays very rapid irreversible inhibition of HRV-14 3CP (k(obs)/[I] = 800 000 M-1 s(-1)) and potent antiviral activity against HRV-14 in cell culture (EC50 = 0.056 mu M). A 1.9 Angstrom crystal structure of an S-alkylthiocarbamate-containing inhibitor complexed with HRV-8 3CP is also detailed.
• An Improved Preparation of 4-Hydroxymethyl-L-Phenylalanine
  作者：Enrico Morera、Giorgio Ortar、Aurelio Varani

  DOI：10.1080/00397919809458709

  日期：1998.11

  Palladium-catalyzed hydroformylation of methyl esters of N-Boc-L-tyrosine triflate (1a) and N-Boc-4-iodo-L-phenylalanine (1b) followed by reduction with sodium borohydride and standard deprotection procedures affords the title compound in 77 and 83% overall yield, respectively.