(S)-6-((tert-butoxycarbonyl)amino)-2-hydroxyhexanoic acid | 111223-31-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-6-((tert-butoxycarbonyl)amino)-2-hydroxyhexanoic acid
• 英文别名: (S)-6-(tert-butyloxycarbonylamino)-2-hydroxyhexanoic acid；N-Boc-(S)-6-amino-2-hydroxyhexanoic acid；L-O-lysine(Boc)-OH；HO-(Boc)Lys-OH；(S)-2-hydroxy-6-(t-butyloxycarbonylamino) hexanoic acid；(S)-2-hydroxy-6-(t-butyloxycarbonylamino)-hexanoic acid；(S)-6-(Boc-amino)-2-hydroxyhexanoic Acid；(2S)-2-hydroxy-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid
• CAS: 111223-31-5
• 化学式: C₁₁H₂₁NO₅
• 分子量: 247.291
• InChiKey: NKQWPQYVVKUEPV-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (S)-6-((tert-butoxycarbonyl)amino)-2-hydroxyhexanoic acid 在 palladium on activated charcoal 偶氮二甲酸二异丙酯 、 氢气 、 caesium carbonate 、 三苯基膦 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， -40.0~20.0 ℃ 、101.33 kPa 条件下， 反应 7.17h， 生成 D-PhthN-O-Lys(Boc)-OH
  参考文献：
  名称：

  由L-氨基酸或L-羟基酸合成光学活性的邻苯二甲酰基D-氨基氧基酸，作为制备氨基氧基肽的基础。

  摘要：

  DOI：

  10.1021/jo0006573
• 作为产物：
  描述：

  N6-Cbz-L-赖氨酸 在 palladium on activated charcoal sodium hydroxide 、 氢气 、 sodium nitrite 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 反应 4.33h， 生成 (S)-6-((tert-butoxycarbonyl)amino)-2-hydroxyhexanoic acid
  参考文献：
  名称：

  由L-氨基酸或L-羟基酸合成光学活性的邻苯二甲酰基D-氨基氧基酸，作为制备氨基氧基肽的基础。

  摘要：

  DOI：

  10.1021/jo0006573

文献信息

• Synthesis of Four Lysine-Linked Cereulide Analogues Showing Ionophoric Activity Towards Potassium Cations as Lead Compounds for Emetic Toxin-Detection by Immunoassays
  作者：Minoru Isobe、Arthit Makarasen、Toshio Nishikawa

  DOI：10.1055/s-0029-1216837

  日期：2009.7

  An improved total synthesis of the emetic toxin cereulide and the preparation of four lysine-linked cereulide analogues is described. The cereulide analogues are prepared by replacing one of the amino acid residues in cereulide with lysine. The cereulide analogues demonstrate ionophoric activity towards alkali metal ions and inorganic ammonium ions, and are currently being used to develop an enzyme-linked immunosorbent assay for cereulide.

  描述了一种改进的呕吐毒素cereulide的总体合成及四种赖氨酸连接的cereulide类似物的制备。cereulide类似物是通过用赖氨酸替换cereulide中的一种氨基酸残基制备的。这些cereulide类似物对碱金属离子和无机铵离子表现出离子载体活性，目前正在用于开发针对cereulide的酶联免疫吸附测定法。
• Facile Removal of Leader Peptides from Lanthipeptides by Incorporation of a Hydroxy Acid
  作者：Noah A. Bindman、Silvia C. Bobeica、Wenshe R. Liu、Wilfred A. van der Donk

  DOI：10.1021/jacs.5b04681

  日期：2015.6.10

  removed in the final step by a protease. Genome mining efforts for new RiPPs are often hampered by the lack of a general method to remove the leader peptides. We describe here the incorporation of hydroxy acids into the precursor peptides in E. coli which results in connection of the leader peptide via an ester linkage that is readily cleaved by simple hydrolysis. We demonstrate the method for two lantibiotics

  核糖体合成和翻译后修饰肽 (RiPP) 天然产物的生物合成通常涉及前体肽，该前体肽含有对修饰过程很重要的前导肽，并在最后步骤中被蛋白酶去除。由于缺乏去除前导肽的通用方法，新 RiPP 的基因组挖掘工作常常受到阻碍。我们在此描述了将羟基酸掺入大肠杆菌中的前体肽中，这导致前导肽通过酯键连接，该酯键很容易通过简单的水解而裂解。我们演示了两种羊毛硫抗生素（乳酸菌素 481 和 nukacin ISK-1）的方法。
• Process for preparing phosphonyloxyacyl amino acids and derivatives
  申请人：——

  公开号：US04885380A1

  公开（公告）日：1989-12-05

  A process is provided for preparing phosphonyloxyacylamino acids and derivatives thereof having the structure ##STR1## wherein ##STR2## which includes the steps of treating a phosphonic acid dichloride of the structure ##STR3## with an .alpha.-hydroxy acid of the structure ##STR4## in the presence of base such as triethylamine at reduced temperatures to form the cyclic mixed anhydride of the structure ##STR5## (which is a new intermediate) and reacting the cyclic mixed anhydride with an amino acid or ester of the structure HX in the presence of base such as triethylamine produces the ACE inhibitor compound ##STR6## In an alternative process, the cyclic anhydride is quenched with water to form the diacid ##STR7## which is treated with a condensing agent such as dicyclohexyl carbodiimide (DCC), 1,1-carbonyldiimidazole (CDI) or thionyl chloride followed by quenching with the amion acid HX produces the above ACE inhibitor compound. In another variation of the process of the invention, the above cyclic anhydride is treated with an alcohol of the structure R.sub.3 OH to form the phosphonic acid diester ##STR8## which may be coupled with the amino acid or ester HX to form the ACE inhibitor ##STR9##

  提供了一种制备磷酸酯氧基酰氨基酸及其衍生物的过程，其结构为##STR1##其中##STR2##包括以下步骤：将结构为##STR3##的磷酸二氯化物与结构为##STR4##的α-羟基酸在碱（如三乙胺）存在下在降温条件下处理，形成结构为##STR5##的环状混合酐（这是一种新的中间体），并在碱（如三乙胺）存在下将环状混合酐与氨基酸或酯结构为HX反应，产生ACE抑制剂化合物##STR6##。在另一种工艺中，环状酐被水淬灭形成二酸##STR7##，该二酸经过与偶氮二环己烷（DCC）、1,1-羰基二咪唑（CDI）或氯化硫酰等缩合剂处理后再与氨基酸HX淬灭形成上述ACE抑制剂化合物。在该发明的另一种变体工艺中，上述环状酐与结构为R.sub.3 OH的醇反应形成磷酸二酯##STR8##，可与氨基酸或酯HX偶联形成ACE抑制剂##STR9##。
• Phosphonic acid derivative having inhibitory activity against carboxypeptidase B
  申请人：Meiji Seika Kaisha Ltd.

  公开号：US20030119787A1

  公开（公告）日：2003-06-26

  A compound represented by the following general formula (I) and a pharmacologically acceptable salt thereof: 1 wherein R 1 represents hydrogen atom, an alkyl group, a substituted alkyl group and the like; R 2 and R 3 represent hydrogen atom, an alkyl group, a substituted alkyl group, an alkoxyl group and the like; X represents —CH 2 —, —O—, or —NH—; A represents the following group (II): 2 [in which R 7 and R 8 represent hydrogen atom, an alkyl group, an acyl group, an alkoxycarbonyl group and the like; R 9 and R 10 represents hydrogen atom, a halogen atom, hydroxyl group, phenyl group, an alkyl group and the like] and the like; and E represents hydrogen atom and the like, which has inhibitory activity against carboxypeptidase B and is useful for therapeutic and/or preventive treatment of a thrombotic disease.

  以下是通用式（I）及其药学上可接受的盐所代表的化合物：其中R1代表氢原子、烷基、取代烷基等；R2和R3代表氢原子、烷基、取代烷基、烷氧基等；X代表—CH2—、—O—或—NH—；A代表以下基团（II）：其中R7和R8代表氢原子、烷基、酰基、烷氧羰基等；R9和R10代表氢原子、卤素原子、羟基、苯基、烷基等；E代表氢原子等，具有对羧肽酶B的抑制活性，可用于治疗和/或预防血栓性疾病。
• PHOSPHONIC ACID DERIVATIVES HAVING CARBOXYPEPTIDASE B INHIBITORY ACTIVITY
  申请人：Meiji Seika Kaisha, Ltd.

  公开号：EP1152004A1

  公开（公告）日：2001-11-07

  A compound represented by the following general formula (I) and a pharmacologically acceptable salt thereof: wherein R1 represents hydrogen atom, an alkyl group, a substituted alkyl group and the like; R2 and R3 represent hydrogen atom, an alkyl group, a substituted alkyl group, an alkoxyl group and the like; X represents -CH2-, -O-, or -NH-; A represents the following group (II): [in which R7 and R8 represent hydrogen atom, an alkyl group, an acyl group, an alkoxycarbonyl group and the like; R9 and R10 represents hydrogen atom, a halogen atom, hydroxyl group, phenyl group, an alkyl group and the like] and the like; and E represents hydrogen atom and the like, which has inhibitory activity against carboxypeptidase B and is useful for therapeutic and/or preventive treatment of a thrombotic disease.

  由以下通式（I）代表的化合物及其药理学上可接受的盐： 其中 R1 代表氢原子、烷基、取代的烷基等；R2 和 R3 代表氢原子、烷基、取代的烷基、烷氧基等；X 代表 -CH2-、-O- 或 -NH-；A 代表以下基团 (II)： [其中 R7 和 R8 代表氢原子、烷基、酰基、烷氧基羰基等；R9 和 R10 代表氢原子、卤素原子、羟基、苯基、烷基等]等；E 代表氢原子等，对羧肽酶 B 具有抑制活性，可用于血栓性疾病的治疗和/或预防。