Boc-Aib-SH

• 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: Boc-Aib-SH
• 英文别名: N-Boc-Aib-SH；2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanethioic S-acid
• 化学式: C₉H₁₇NO₃S
• 分子量: 219.305
• InChiKey: KAKDCQVOCHUHGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  56.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Boc-Aib-SH 在 碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 12.0h， 以0.54 g的产率得到2-((tert-butoxycarbonyl)amino)-2-methylpropanoic dithioperoxyanhydride
  参考文献：
  名称：

  Thioacetic Acid/NaSH-Mediated Synthesis of N-Protected Amino Thioacids and Their Utility in Peptide Synthesis

  摘要：

  Thioacids are recently gaining momentum due to their versatile reactivity. The reactivity of thioacids has been widely explored in the selective amide/peptide bond formation. Thioacids are generally synthesized from the reaction between activated carboxylic acids such as acid chlorides, active esters, etc., and Na2S, H2S, or NaSH. We sought to investigate whether the versatile reactivity of the thioacids can be tuned for the conversion of carboxylic acids into corresponding thioacids in the presence of NaSH. Herein, we report that thioacetic acid- and NaSH-mediated synthesis of N-protected amino thioacids from the corresponding N-protected amino acids, oxidative dimerization of thioacids, crystal conformations of thioacid oxidative dimers, and the utility of thioacids and oxidative dimers in peptide synthesis. Our results suggest that peptides can be synthesized without using standard coupling agents.

  DOI：

  10.1021/jo402872p
• 作为产物：
  描述：

  N-叔丁氧羰基-2-甲基丙氨酸 在 sodium sulfide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以86%的产率得到Boc-Aib-SH
  参考文献：
  名称：

  Facile N-Urethane-Protected α-Amino/Peptide Thioacid Preparation Using EDC and Na2S

  摘要：

  本文报道了一种高效的方法，通过EDC和Na2S介导，从相应的酸合成N-urethane保护的α-氨基酸/肽硫酸酯。在温和条件下快速反应使得该过程能在较短时间内完成，且产率良好，无需柱层析纯化。该化学方法适用于多种urethane保护基团、侧链功能团以及空间位阻氨基酸。

  DOI：

  10.1055/s-0031-1290091

文献信息

• Facile N-Urethane-Protected α-Amino/Peptide Thioacid Preparation Using EDC and Na2S
  作者：Vommina Sureshbabu、T. Vishwanatha、M. Samarasimhareddy

  DOI：10.1055/s-0031-1290091

  日期：2012.1

  We report herein an efficient protocol for the synthesis of N-urethane-protected α-amino/peptide thioacids from their corresponding acids mediated by EDC and Na2S. The fast reaction under mild conditions enabled the process to be completed in shorter duration with good yield circumventing column purification. The chemistry is compatible with a wide variety of urethane protecting groups, side-chain functionalities, and sterically hindered amino ­acids.

  本文报道了一种高效的方法，通过EDC和Na2S介导，从相应的酸合成N-urethane保护的α-氨基酸/肽硫酸酯。在温和条件下快速反应使得该过程能在较短时间内完成，且产率良好，无需柱层析纯化。该化学方法适用于多种urethane保护基团、侧链功能团以及空间位阻氨基酸。
• Epimerization-Free Block Synthesis of Peptides from Thioacids and Amines with the Sanger and Mukaiyama Reagents
  作者：David Crich、Indrajeet Sharma

  DOI：10.1002/anie.200805782

  日期：2009.3.16

  reaction of C‐terminal thioacids derived from protected amino acids and peptides with the Sanger reagent and other electron‐deficient aryl halides in the presence of a free amine immediately form a peptide bond with the amine. This essentially epimerization‐free method was used for the 4+4 block synthesis of a hindered octapeptide (see scheme; Boc, Pbf, and Trt are protecting groups).

  在游离胺存在下，由受保护氨基酸和肽衍生的C末端硫代酸与Sanger试剂和其他电子不足的芳基卤化物快速反应而形成的高活化硫酯立即与胺形成肽键。该基本无差向异构的方法用于受阻八肽的4 + 4嵌段合成（请参阅方案； Boc，Pbf和Trt是保护基）。
• A traceless approach to amide and peptide construction from thioacids and dithiocarbamate-terminal amines
  作者：Wenteng Chen、Jiaan Shao、Miao Hu、Wanwan Yu、Marc A. Giulianotti、Richard A. Houghten、Yongping Yu

  DOI：10.1039/c2sc21317f

  日期：——

  with a range of unprotected side chains of amino acid. The ability to produce amide or peptides by a traceless removal of the auxiliary is a significant virtue of the method. Meanwhile, the application of this new peptide-bond-forming reaction to the synthesis of novel endomorphin (EM) derivatives with various binding potencies was realized.

  已经设计出一种新颖且无痕的策略，其允许将硫代酸和二硫代氨基甲酸酯末端的胺偶联。在较早的天然化学连接方法中，已假定该策略取决于半胱氨酸侧链功能等同物的附着。这种方法能够无痕地去除CS 2以直接生成所需的酰胺键，并且与一系列未保护的氨基酸侧链兼容。通过无痕去除助剂产生酰胺或肽的能力是该方法的重要优点。同时，实现了这种新的肽键形成反应在具有各种结合力的新型内啡肽（EM）衍生物的合成中的应用。
• ANTIVIRAL ALIPHATIC ESTER PRODRUGS OF TENOFOVIR
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20180179208A1

  公开（公告）日：2018-06-28

  Compounds of Formula I: and their pharmaceutically acceptable salts are useful for the inhibition of HIV reverse transcriptase. The compounds may also be useful for the prophylaxis or treatment of infection by HIV and in the prophylaxis, delay in the onset or progression, and treatment of AIDS. The compounds and their salts can be employed as ingredients in pharmaceutical compositions, optionally in combination with other antiviral agents, immunomodulators, antibiotics or vaccines

  公式I的化合物及其药用盐对于抑制HIV逆转录酶具有用处。这些化合物也可能对预防或治疗HIV感染以及预防、延缓爱滋病的发作或进展以及治疗方面具有用处。这些化合物及其盐可作为药物组合物中的成分，可选择性地与其他抗病毒药物、免疫调节剂、抗生素或疫苗组合使用。
• Processes For Forming Amide Bonds And Compositions Related Thereto
  申请人：Liebeskind Lanny S.

  公开号：US20120107902A1

  公开（公告）日：2012-05-03

  The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.

  本披露涉及生产酰胺键的方法及相关试剂。在某些实施例中，本披露涉及生产酰胺的方法，包括混合O-硅基硫代酯和胺，以形成酰胺。在另一实施例中，本披露涉及混合硫酸、硅基化试剂和胺的方法，以形成酰胺。