(R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-mercaptopropanoate | 92278-78-9

• 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)-benzyl 2-((tert-butoxycarbonyl)amino)-3-mercaptopropanoate
• 英文别名: N-tert-butoxycarbonyl-L-cysteine benzyl ester；Boc-Cys-OBn；Boc-L-Cys-OBn；benzyl (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-sulfanylpropanoate
• CAS: 92278-78-9
• 化学式: C₁₅H₂₁NO₄S
• 分子量: 311.402
• InChiKey: LHAIORAWSORWRF-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  65.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-mercaptopropanoate 在 bismuth(III) chloride 作用下， 以 水 、 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到L-cysteine benzyl ester
  参考文献：
  名称：

  Chemoselective deprotection of N-Boc group in amino acids and peptides by bismuth(III) trichloride

  摘要：

  Selective deprotection of N-Boc group was achieved in excellent yields using bismuth(111) trichloride in a mixed solvent of acetonitrile and water (50: 1, v/v) at 55 degrees C. Acid-labile groups such as Pine and tert-butyl ester were not affected and no alkylation of tryptophan, methionine, and cysteine residues was observed under the deprotection conditions. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.003
• 作为产物：
  描述：

  N,N'-双(叔丁氧羰基)-L-胱氨酸 在 草酰氯 、 三丁基膦 、 水 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (R)-benzyl 2-((tert-butoxycarbonyl)amino)-3-mercaptopropanoate
  参考文献：
  名称：

  立体保护的正交保护的α-甲基降冰片氨酸的合成。

  摘要：

  [反应：请参阅文本]由于以前已经将不常见的氨基酸降冰硫氨酸（nor-Lan）掺入羊毛硫菌素乳链菌肽C环的环状肽类似物中，因此我们在此报告了新（S，R）-和（ R，R）-α-甲基降冰片氨酸（α-Me-nor-Lan）。还制备了这些化合物的正交保护的衍生物。合成这些双氨基酸的关键步骤是相应的环状氨基磺酸盐与带有适当保护的1-半胱氨酸衍生物的SH基团的S（N）2开环反应。

  DOI：

  10.1021/ol060993r

文献信息

• Glycoprotein Semisynthesis by Chemical Insertion of Glycosyl Asparagine Using a Bifunctional Thioacid-Mediated Strategy
  作者：Kota Nomura、Yuta Maki、Ryo Okamoto、Ayano Satoh、Yasuhiro Kajihara

  DOI：10.1021/jacs.1c02601

  日期：2021.7.14

  thioacid-mediated strategy, which can couple two peptides with the N- and C-termini of glycosyl asparagine thioacid. Previous glycoprotein synthesis methods required valuable glycosyl asparagine in the early stage and subsequent multiple glycoprotein synthesis routes, whereas the developed concept can generate glycoproteins within a few steps from peptide and glycosyl asparagine thioacid. Herein, we report the characterization

  糖基化是分泌蛋白和细胞表面蛋白的主要修饰，由此产生的聚糖在其结构中表现出相当大的异质性。要了解每种糖型产生的生物学过程，制备均质糖蛋白对于广泛的生物学实验至关重要。为了建立一种更加稳健和快速的合成均质糖蛋白的合成路线，我们研究了几个基于氨基硫代酸的关键反应。我们发现与糖基天冬酰胺硫代酸和肽硫代酸形成的二酰基二硫键偶联 (DDC) 产生糖肽。这种高效的偶联反应使我们能够开发一种新的糖蛋白合成方法，例如双功能硫代酸介导的策略，该方法可以将两个肽与糖基天冬酰胺硫代酸的 N 端和 C 端偶联。以前的糖蛋白合成方法在早期需要有价值的糖基天冬酰胺和随后的多种糖蛋白合成路线，而开发的概念可以在几个步骤内从肽和糖基天冬酰胺硫代酸中生成糖蛋白。在这里，我们报告了氨基硫代酸的 DDC 的表征和糖基天冬酰胺硫代酸用于稳健糖蛋白半合成的有效能力。
• Efficient Synthesis of Differently Protected Lanthionines viaβ-Bromoalanine Derivatives
  作者：Xiangming Zhu、Richard R. Schmidt

  DOI：10.1002/ejoc.200300336

  日期：2003.10

  Lanthionines, thioether-linked alanines, are readily available from differently protected β-bromoalanine and cysteine derivatives under phase-transfer conditions at pH 8.5. Racemisation or elimination of starting materials or products was not observed. Also base-sensitive protecting groups, such as, for instance, the Fmoc group, were compatible with this procedure, thus conveniently permitting the

  羊毛硫氨酸，硫醚连接的丙氨酸，在 pH 8.5 的相转移条件下很容易从不同保护的 β-溴丙氨酸和半胱氨酸衍生物中获得。未观察到起始材料或产物的外消旋或消除。碱敏感的保护基团，例如 Fmoc 基团，也与该程序兼容，因此可以方便地合成正交保护的羊毛硫氨酸。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Processes for producing optically active 2-amino-1-phenylethanol derivatives
  申请人：Daicel Chemical Industries, Ltd.

  公开号：US20030143701A1

  公开（公告）日：2003-07-31

  An (R)-2-amino-1-phenylethanol derivative shown by the general formula (IIa) 1 wherein R 1 and R 5 represent a hydrogen atom, etc.; R 2 , R 3 and R 4 independently represent a halogen atom, etc., or a salt thereof, can readily be produced (1) by permitting a microorganism belonging to the genus Rhodosporidium, the genus Comamonas or the like to act on a mixture of corresponding (R)-form and (S)-form to asymmetrically utilize, or (2) by permitting a microorganism belonging to the genus Lodderomyces, the genus Pilimelia or the like to act on a corresponding aminoketone derivative to asymmetrically reduce. An (R,R)-1-phenyl-2-[(2-phenyl-1-alkylethyl)amino]ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (IIa) or a salt thereof. Said derivative is useful as an intermediate for producing an anti-obesity agent and so on.

  通式（IIa）所示的（R）-2-氨基-1-苯乙醇衍生物，其中R1和R5代表氢原子等；R2、R3和R4分别独立地表示卤素原子等，或其盐，可以通过（1）让属于红孢霉属、普通小杆菌属或类似菌属的微生物作用于相应（R）-型和（S）-型的混合物以不对称利用，或（2）让属于洛德罗霉属、皮利米利亚属或类似菌属的微生物作用于相应的氨基酮衍生物以不对称还原而轻松制备。可以从式（IIa）化合物或其盐中轻松获得具有高光学纯度的（R，R）-1-苯基-2-［（2-苯基-1-烷基乙基）氨基］乙醇衍生物。所述衍生物可用作生产抗肥胖剂等中间体。
• Synthesis of Novel <i>S</i>-Neoglycopeptides from Glycosylthiomethyl Derivatives
  作者：Xiangming Zhu、Kandasamy Pachamuthu、Richard R. Schmidt

  DOI：10.1021/ol036186z

  日期：2004.4.1

  Reaction of glycosylthiomethyl azides with amino acid and peptide derivatives containing aspartate and glutamate thio acids gave the corresponding glycosylthiomethyl amides in excellent yields. Another type of neoglycopeptides was obtained via reaction of glycosylthiomethyl bromide with cysteine and homocysteine containing peptide derivatives, thus affording the corresponding S-(glycosylthiomethyl) peptides.
• Identification and immunological evaluation of novel TLR2 agonists through structure optimization of Pam3CSK4
  作者：Xinming Du、Jiawen Qian、Yujie Wang、Mingming Zhang、Yiwei Chu、Yingxia Li

  DOI：10.1016/j.bmc.2019.05.005

  日期：2019.7

  Toll-like receptor 2 (TLR2) is a bridge between innate immunity and adaptive immunity. TLR2 agonists have been exploited as potential vaccine adjuvants and antitumor agents. However, no TLR2 agonists have been approved by FDA up to now. To discover drug-like TLR2 selective agonists, a novel series of Pam3CSK4 derivatives were designed based on the crystal structure of hTLR2-hTLR1-Pam(3)CSK(4) complex, synthesized and evaluated for their immune-stimulatory activities. Among them, 35c was identified as a murine-specific TLR2 agonist, while 35f was a human-specific TLR2 agonist. Besides, 35d (human and murine TLR2 agonist) showed TLR2 agonistic activity comparable to Pam3CSK4, which included: elevated IL-6 expression level (EC50= 83.08 +/- 5.94 nM), up-regulated TNF-alpha and IL-6 mRNA expression and promoted maturation of DCs through activating the NF-kappa B signaling pathway. TLRs antibodies test showed that 35a and 35d were TLR2/1 agonists, while 35f was a TLR2/6 agonist.