Fmoc-Ala-Cys-Leu-NH2 | 1403825-93-3

• 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: Fmoc-Ala-Cys-Leu-NH2
• CAS: 1403825-93-3
• 化学式: C₂₇H₃₄N₄O₅S
• 分子量: 526.657
• InChiKey: SWJUQQJSWKXZLU-GMWOSMDTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.34
• 重原子数：
  37.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  139.62
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  9H-fluoren-9-ylmethyl N-[(2S)-1-[[(2R)-1-[[(2S)-1-amino-4-methyl-1-oxopentan-2-yl]amino]-3-[(4-methoxy-2,6-dimethylphenyl)methylsulfanyl]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]carbamate 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 水 为溶剂， 反应 0.5h， 生成 Fmoc-Ala-Cys-Leu-NH2
  参考文献：
  名称：

  Acid-Labile Cys-Protecting Groups for the Fmoc/tBu Strategy: Filling the Gap

  摘要：

  To address the existing gap in the current set of acid-labile Cys-protecting groups for the Fmoc/fBu strategy, diverse Fmoc-Cys(PG)-OH derivatives were prepared and incorporated into a model tripeptide to study their stability against TFA. S-Dpm proved to be compatible with the commonly used S-Trt group and was applied for the regioselecive construction of disulfide bonds.

  DOI：

  10.1021/ol302550p

文献信息

• Tetrahydropyranyl, a Nonaromatic Acid-Labile Cys Protecting Group for Fmoc Peptide Chemistry
  作者：Iván Ramos-Tomillero、Hortensia Rodríguez、Fernando Albericio

  DOI：10.1021/acs.orglett.5b00444

  日期：2015.4.3

  Tetrahydropyranyl (Thp), which exploits the concept of being an S,O-acetal nonaromatic protecting group for cysteine, has been shown to be superior to Trt, Dpm, Acm, and StBu in solid-phase peptide synthesis using the Fmoc/tBu strategy. Thus, Cys racemization and C-terminal 3-(1-piperidinyl)alanine formation were minimized when the Cys was protected with Thp. This nonaromatic protecting group also

  四氢吡喃基（THP），其利用的是一个概念小号，ö -acetal非芳香族保护基为半胱氨酸，已被证明优于TRT，DPM，ACM，和S吨在使用Fmoc固相肽合成BU / t Bu策略。因此，当Cys被Thp保护时，Cys外消旋作用和C末端3-（1-哌啶基）丙氨酸的形成被最小化。该非芳族保护基团还改善了含Cys的被保护肽的溶解性。
• 2-(Dibenzylamino)butane-1,4-dithiol (DABDT), a Friendly Disulfide-Reducing Reagent Compatible with a Broad Range of Solvents
  作者：Sinenhlanhla N. Mthembu、Anamika Sharma、Fernando Albericio、Beatriz G. de la Torre

  DOI：10.1021/acs.orglett.9b04106

  日期：2019.12.20

  Disulfide-reducing agents play a crucial role in bioconjugate chemistry. Herein, we describe the synthesis of a new disulfide-reducing agent [2-(dibenzylamino)butane-1,4-dithiol (DABDT)] that is conveniently prepared from inexpensive aspartic acid. Being nonmalodorous and highly soluble in a broad range of solvents, DABDT is user-friendly. We have demonstrated its performance both in solution and in the solid phase.