(2S)-tert-butoxycarbonylamino-4-hydroxybutanoic acid allyl ester | 475150-35-7

• 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: (2S)-tert-butoxycarbonylamino-4-hydroxybutanoic acid allyl ester
• 英文别名: allyl 2-(N-tert-butoxycarbonyl)amino-4-hydroxybutanoate；Nα-Boc-Hse-OAllyl；Boc-Hse-OAll；(+/-)-N-(tert-butoxycarbonyl)homoserine allyl ester；prop-2-enyl (2S)-4-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 475150-35-7
• 化学式: C₁₂H₂₁NO₅
• 分子量: 259.302
• InChiKey: HWCVCVCOXNERCA-VIFPVBQESA-N

物化性质

• 沸点：
  388.8±42.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-tert-butoxycarbonylamino-4-hydroxybutanoic acid allyl ester 在 咪唑 、 碘 、 1-羟基苯并三唑 、 caesium carbonate 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 allyl (S)-4-[(R)-2-(S)-2-{[(9H-fluoren-9-yl)methoxycarbonyl]amino}propanamido-3-ethoxy-3-oxopropylsulfanyl]-2-[(tert-butoxycarbonyl)amino]butanoate
  参考文献：
  名称：

  Novel thiol- and thioether-containing amino acids: cystathionine and homocysteine families

  摘要：

  Natural l-homocysteine and l,l-cystathionine, along with a series of unnatural analogues, have been prepared from l-aspartic and l-glutamic acid. Manipulation of the protected derivatives provided omega-iodoamino acids, which were used in thioalkylation reactions of sulfur nucleophiles, such as the ester of l-cysteine and potassium thioacetate.

  DOI：

  10.1007/s00726-012-1352-5
• 作为产物：
  描述：

  Boc-Asp-OAll 在 N-甲基吗啉 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.25h， 生成 (2S)-tert-butoxycarbonylamino-4-hydroxybutanoic acid allyl ester
  参考文献：
  名称：

  Novel thiol- and thioether-containing amino acids: cystathionine and homocysteine families

  摘要：

  Natural l-homocysteine and l,l-cystathionine, along with a series of unnatural analogues, have been prepared from l-aspartic and l-glutamic acid. Manipulation of the protected derivatives provided omega-iodoamino acids, which were used in thioalkylation reactions of sulfur nucleophiles, such as the ester of l-cysteine and potassium thioacetate.

  DOI：

  10.1007/s00726-012-1352-5

文献信息

• Synthesis of Peptide Disulfide-Bond Mimics by Using Fully Orthogonally Protected Diaminodiacids
  作者：Tao Wang、Jian Fan、Xiao-Xu Chen、Rui Zhao、Yang Xu、Donald Bierer、Lei Liu、Yi-Ming Li、Jing Shi、Ge-Min Fang

  DOI：10.1021/acs.orglett.8b02459

  日期：2018.10.5

  A new strategy was developed for the synthesis of peptide disulfide-bond mimics using fully orthogonally protected diaminodiacids. This method overcomes the previous problems of heavy-metal contamination and poor compatibility with Fmoc chemistry and provides a practical avenue for the efficient preparation of peptide disulfide-bond mimics.

  开发了一种使用完全正交保护的二氨基二酸合成肽二硫键模拟物的新策略。该方法克服了先前的重金属污染和与Fmoc化学相容性差的问题，并为有效制备肽二硫键模拟物提供了实用途径。
• Inhibition of Glyoxalase I: The First Low-Nanomolar Tight-Binding Inhibitors
  作者：Swati S. More、Robert Vince

  DOI：10.1021/jm900382u

  日期：2009.8.13

  -based glyoxalase I inhibitors culminated in the discovery of the first single-digit nanomolar inhibitor. This study makes available key information about possible means to address the issues of metabolic instability, low potency, and synthetic complexicity that have plagued the area of glyoxalase I inhibition. Knowledge garnered from this study has implications in the design of inhibitors with higher

  对已知的基于S-（N-芳基-N-羟基氨基甲酰基）谷胱甘肽的乙二醛酶I抑制剂的结构进行了一系列合理的修改，最终发现了第一个个位数的纳摩尔抑制剂。这项研究提供了有关解决困扰乙二醛酶I抑制区域的代谢不稳定，药效低和合成复杂性问题的可能手段的关键信息。从这项研究中获得的知识对具有更高构象定义和更低肽特性的抑制剂的设计具有重要意义。
• A Versatile Set of Aminooxy Amino Acids for the Synthesis of Neoglycopeptides
  作者：Michael R. Carrasco、Ryan T. Brown

  DOI：10.1021/jo034984x

  日期：2003.11.1

  N-alkylaminooxy amino acids have been synthesized in 22-56% overall yield from readily available amino acid precursors. Each amino acid can be efficiently incorporated into peptides using Boc-chemistry-based solid-phase peptide synthesis, and in three of the four cases the resulting peptides can be chemoselectively glycosylated at the aminooxy side chains to generate neoglycopeptides. The range of N-alkylaminooxy

  已经从容易获得的氨基酸前体以22-56％的总产率合成了四种N-烷基氨基氧基氨基酸。可以使用基于Boc化学的固相肽合成方法将每种氨基酸有效地掺入肽中，并且在四种情况中的三种中，可以将所得肽在氨氧基侧链上进行化学选择性糖基化以生成新糖肽。制备的N-烷基氨基氧基氨基酸范围允许糖与肽骨架的连接距离为两个，三个或四个原子，并且每个糖都确保连接的糖采用环状构象。这些衍生物为生物相关的新糖肽阵列提供了便捷途径，这些新糖肽可用于探测连接的糖对肽和蛋白质的结构和功能的影响。
• Synthesis of neoglycopeptides by chemoselective reaction of carbohydrates with peptides containing a novel N′-methyl-aminooxy amino acid
  作者：Michael R Carrasco、Michael J Nguyen、Dawn R Burnell、Michael D MacLaren、Shawna M Hengel

  DOI：10.1016/s0040-4039(02)01212-1

  日期：2002.8

  N′-methyl-aminooxy amino acid has been designed, synthesized, and successfully incorporated into peptides using standard solid-phase peptide synthesis procedures. Reaction of these peptides with native reducing sugars yields neoglycopeptides via a chemoselective reaction with the aminooxy side chains. The key feature of the new amino acid is that it maintains attached sugars in their cyclic conformations and close

  已经使用标准的固相肽合成方法设计，合成了新的N'-甲基-氨基氧基氨基酸，并成功地将其掺入了肽中。这些肽与天然还原糖的反应通过与氨氧基侧链的化学选择性反应产生新糖肽。新氨基酸的关键特征是它使附着的糖保持其环状构象并靠近肽主链。
• Sulfonamide derivatives
  申请人：Sankyo Company, Limited

  公开号：US06673804B1

  公开（公告）日：2004-01-06

  A compound of the formula (I) or a pharmacologically acceptable salt, ester or other derivative thereof: R1 is H or NHOH. R2 is H, optionally substituted alkyl, cycloalkyl or a group —AR6. A is an alkylene which may be optionally interrupted by O, —S(O)m— or —N(R9). R6 is a group (II), (III), (IV) X is O, S, —N(R10)—, —C(R11)(R12)—. Y is O, CO, —S(O)n—, —N(R10)—, —C(R11)(R12)—. Each of R7 and R8 is H, alkyl, COOH, optionally substituted alkyl, etc. Each of R9, R10, R11, and R12 is H, alkyl, etc. Each of m and n is 0 to 2. R3 is H, optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted alkenyl, optionally substituted alkynyl. R4 is optionally substituted (hetero)arylene. R5 is optionally substituted alkyl, optionally substituted (hetero)aryl. These compounds have matrixmetalloproteinase—13 inhibitory activity and aglycanase inhibitory activity.

  化合物的公式（I）或其药理学上可接受的盐，酯或其他衍生物：其中，R1为H或NHOH，R2为H，可选择性地取代的烷基，环烷基或群体-AR6，A为可选择性地由O，-S（O）m-或-N（R9）中断的烷基，R6为群体（II），（III），（IV），X为O，S，-N（R10）-，-C（R11）（R12）-，Y为O，CO，-S（O）n-，-N（R10）-，-C（R11）（R12）-，R7和R8中的每一个为H，烷基，COOH，可选择性取代的烷基等，R9，R10，R11和R12中的每一个为H，烷基等，m和n中的每一个为0到2，R3为H，可选择性取代的烷基，可选择性取代的环烷基，可选择性取代的烯基，可选择性取代的炔基，R4为可选择性取代的（杂）芳基，R5为可选择性取代的烷基，可选择性取代的（杂）芳基。这些化合物具有基质金属蛋白酶-13抑制活性和去糖基酶抑制活性。