(R)-homotyrosine | 749828-81-7

• 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: (R)-homotyrosine
• 英文别名: homo-p-(R)-tyrosine；D-homotyrosine；D-Htyr；(R)-2-Amino-4-(4-hydroxyphenyl)butanoic acid；(2R)-2-amino-4-(4-hydroxyphenyl)butanoic acid
• CAS: 749828-81-7
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: LOOZZTFGSTZNRX-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  88
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-homotyrosine 在 盐酸 、 硫酰氟 、 sodium tetraborate decahydrate 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 C₁₀H₁₂FNO₅S*ClH
  参考文献：
  名称：

  Semisynthesis of a Bacterium with Non-canonical Cell-Wall Cross-Links

  摘要：

  The cell wall is an elaborate framework of peptidoglycan that serves to protect the bacterium against osmotic challenge. This exoskeleton is composed of repeating saccharides covalently cross-linked by peptide stems. The general structure of the cell wall is widely conserved across diverse Gram-negative bacteria. To begin to explore the biological consequence of introducing non-canonical cross-links into the cell wall of Escherichia coli, we generated a bacterium where up to 31% of the cell-wall cross-links are formed by a non-enzymatic reaction between a sulfonyl fluoride and an amino group. Bacteria with these noncanonical cell-wall cross-links achieve a high optical density in culture, divide and elongate successfully, and display no loss of outer membrane integrity. This work represents a first step in the design of bacteria with non-canonical "synthetic" cell walls.

  DOI：

  10.1021/jacs.0c02956
• 作为产物：
  描述：

  methyl (2R)-4-(4-hydroxyphenyl)-4-oxo-2-[(2,2,2-trifluoroacetyl)amino]butanoate 在 盐酸 、 10% palladium on activated carbon 、 水 、 氢气 、 溶剂黄146 作用下， 反应 7.0h， 生成 (R)-homotyrosine
  参考文献：
  名称：

  三氟甲磺酸中苯酚和酰氯的O-酰化和Friedel-Crafts酰化的比较以及苯酯的Fries重排：光学活性同酪氨酸的有效合成

  摘要：

  对于酸性条件下的竞争性O-酰化和C-酰化（Friedel-Crafts酰化和Fries重排），必须控制涉及酚衍生物和酰氯的反应。检查了在用作催化剂和溶剂的三氟甲磺酸（TfOH）中这些反应的程度。尽管有效的O-酰化需要稀释的TfOH，但在温和的条件下有效的C-酰化则需要浓缩的TfOH。这些结果已应用于新的高酪氨酸衍生物的合成。N -TFA–Asp（OBn）–OMe的弗里斯重排和苯酚与N的Friedel-Crafts酰化反应TfOH中的-TFA–Asp（Cl）–OMe提供高酪氨酸骨架，然后还原和脱保护得到高酪氨酸，以光学纯净形式保留Asp的立体化学。

  DOI：

  10.1016/j.tet.2010.11.047

文献信息

• Homotyrosine-Containing Cyanopeptolins 880 and 960 and Anabaenopeptins 908 and 915 from <i>Planktothrix agardhii</i> CYA 126/8
  作者：Hilary S. Okumura、Benjamin Philmus、Cyril Portmann、Thomas K. Hemscheidt

  DOI：10.1021/np800557m

  日期：2009.1.23

  Two homotyrosine-bearing cyanopeptolins are described from Planktothrix agardhii CYA 126/8. The compounds feature a common homotyrosine-containing cyclohexadepsipeptide and differ by sulfation of an exocyclically located 2-O-methyl-D-glyceric acid residue. In addition we describe two anabaenopeptins, which contain two homotyrosine residues, one of which is N-methylated. The anabaenopeptins have a common cyclopentapeptide portion and differ in the amino acid linked to it via an ureido bond, arginine and tyrosine, respectively.
• US7253194B2
  申请人：——

  公开号：US7253194B2

  公开（公告）日：2007-08-07
• [EN] SPIRO PIPERIDINES AND HOMOLOGS PROMOTE RELEASE OF GROWTH HORMONE<br/>[FR] SPIRO PIPERIDINES ET COMPOSES HOMOLOGUES FAVORISANT LA LIBERATION DE L'HORMONE DE CROISSANCE
  申请人：MERCK & CO., INC.

  公开号：WO1994019367A1

  公开（公告）日：1994-09-01

  (EN) There are disclosed certain novel compounds identified as spiro piperidines and homologs which promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such spiro compounds as the active ingredient thereof are also disclosed.(FR) La découverte porte sur certains composés nouveaux identifiés comme étant des spiro pipéridines et leurs homologues qui favorisent la libération de l'hormone de croissance chez l'homme et chez l'animal. Cette propriété peut servir à favoriser la croissance d'animaux d'élevage pour augmenter le rendement de la production de produits carnés, et chez l'homme, à traiter des situations physiologiques ou médicales telles qu'une petite taille chez les enfants présentant un déficit en hormone de croissance, ou à traiter des situations médicales qui s'améliorent de par les effets anabolisants de l'hormone de croissance. La découverte porte aussi sur d'autres compositions dont de tels composés de type spiro sont le principe actif et qui agissent sur la libération de l'hormone de croissance.
• Comparisons of O-acylation and Friedel–Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: effective synthesis of optically active homotyrosines
  作者：Ryo Murashige、Yuka Hayashi、Syo Ohmori、Ayuko Torii、Yoko Aizu、Yasuyuki Muto、Yuta Murai、Yuji Oda、Makoto Hashimoto

  DOI：10.1016/j.tet.2010.11.047

  日期：2011.1

  Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel–Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH

  对于酸性条件下的竞争性O-酰化和C-酰化（Friedel-Crafts酰化和Fries重排），必须控制涉及酚衍生物和酰氯的反应。检查了在用作催化剂和溶剂的三氟甲磺酸（TfOH）中这些反应的程度。尽管有效的O-酰化需要稀释的TfOH，但在温和的条件下有效的C-酰化则需要浓缩的TfOH。这些结果已应用于新的高酪氨酸衍生物的合成。N -TFA–Asp（OBn）–OMe的弗里斯重排和苯酚与N的Friedel-Crafts酰化反应TfOH中的-TFA–Asp（Cl）–OMe提供高酪氨酸骨架，然后还原和脱保护得到高酪氨酸，以光学纯净形式保留Asp的立体化学。
• Semisynthesis of a Bacterium with Non-canonical Cell-Wall Cross-Links
  作者：David A. Dik、Nan Zhang、Jason S. Chen、Bill Webb、Peter G. Schultz

  DOI：10.1021/jacs.0c02956

  日期：2020.6.24

  The cell wall is an elaborate framework of peptidoglycan that serves to protect the bacterium against osmotic challenge. This exoskeleton is composed of repeating saccharides covalently cross-linked by peptide stems. The general structure of the cell wall is widely conserved across diverse Gram-negative bacteria. To begin to explore the biological consequence of introducing non-canonical cross-links into the cell wall of Escherichia coli, we generated a bacterium where up to 31% of the cell-wall cross-links are formed by a non-enzymatic reaction between a sulfonyl fluoride and an amino group. Bacteria with these noncanonical cell-wall cross-links achieve a high optical density in culture, divide and elongate successfully, and display no loss of outer membrane integrity. This work represents a first step in the design of bacteria with non-canonical "synthetic" cell walls.