N,N'-di-tert-butoxycarbonyl-L-cystine dibenzyl ester | 92278-77-8

• 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: N,N'-di-tert-butoxycarbonyl-L-cystine dibenzyl ester
• 英文别名: (2R,2'R)-dibenzyl 3,3'-disulfanediylbis(2-((tert-butoxycarbonyl)amino)propanoate)；(2R,2'R)-dibenzyl 3,3'-disulfanediylbis(2-((tert-butyloxycarbonyl)amino)propanoate)
• CAS: 92278-77-8
• 化学式: C₃₀H₄₀N₂O₈S₂
• 分子量: 620.788
• InChiKey: HUFSGPVKFJJRKV-ZEQRLZLVSA-N

物化性质

• 沸点：
  731.7±60.0 °C(Predicted)
• 密度：
  1.223±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.64
• 重原子数：
  42.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  129.26
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  N,N'-di-tert-butoxycarbonyl-L-cystine dibenzyl ester 在 三丁基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 39.5h， 生成
  参考文献：
  名称：

  [EN] FUNCTIONALIZED HUMAN MILK OLIGOSACCHARIDES AND METHODS FOR PRODUCING THEM
  [FR] OLIGOSACCHARIDES DE LAIT MATERNEL FONCTIONNALISÉS ET LEURS PROCÉDÉS DE PRODUCTION

  摘要：

  New derivatives of human milk oligosaccharides and methods for preparing them are disclosed. Also described herein are hST6GALNAC V and hGCNT2-B variants, along with polynucleotides encoding the variants and host cells comprising the polynucleotides. Further provided herein are reaction mixtures comprising the hST6GALNAC V and hGCNT2-B variants.

  公开号：

  WO2023141513A2
• 作为产物：
  描述：

  L-胱氨酸 在 potassium carbonate 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 N,N'-di-tert-butoxycarbonyl-L-cystine dibenzyl ester
  参考文献：
  名称：

  Identification and immunological evaluation of novel TLR2 agonists through structure optimization of Pam3CSK4

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2019.05.005

文献信息

• Direct Disulfide Formation from 2-Quinolinylmethyl Thioethers with Iron(III) or Copper(II) Salt
  作者：Hidenori Yoshizawa、Akira Otaka、Hiromu Habashita、Nobutaka Fujii

  DOI：10.1246/cl.1993.803

  日期：1993.5

  2-Quinolinylmethyl thioethers were efficiently cleaved to generate the corresponding symmetrical disulfides using the following systems; FeCl3/N,N-dimethylformamide (DMF)/H2O, FeCl3/ethanol (EtOH)/H2O, and CuCl2/DMF/H2O. The 2-quinolinylmethyl group was utilized as a thiol protecting group in the synthesis of a model peptide.

  使用以下系统有效地裂解 2-喹啉基甲基硫醚以生成相应的对称二硫化物；FeCl3/N,N-二甲基甲酰胺 (DMF)/H2O、FeCl3/乙醇 (EtOH)/ 和 CuCl2/DMF/ 。在模型肽的合成中，2-喹啉基甲基被用作硫醇保护基团。
• Synthesis of aS-(Carboxymethyl)cysteine Analog of (L-2-Amino-6-adipyl)-L-cysteinyl-D-valine and its Cell Free Biosynthetic Conversion into 6-[2-(D-2-Amino-2-carboxyethyl)thio) acetamido]penicillanic Acid
  作者：James E. Shields、Charles S. Campbell、Dale C. Duckworth、Norbert Neuss、Steven W. Queener

  DOI：10.1002/hlca.19840670328

  日期：1984.5.2

  A new tripeptide (dimer), bis[(L-cysteine-S-acetyl)-L-hemicystinyl(S2 S2)-D-valine] (6) was synthesized by coupling N-(tert-butoxycarbonyl)-S-carboxymethyl-L-cysteine benzyl ester (1) with S-trityl-L-cysteinyl-D-valine benzyl ester and subsequent removal of the protecting groups. After reduction of the disulfide, the free tripeptide Cys (CH2CO-Cys-D-Val) (Ib) was used as a substrate of isopenicillin-N

  通过偶联N-（叔丁氧羰基）-S-合成了一种新的三肽（二聚体）双[（L-半胱氨酸-S-乙酰基）-L-半胱氨酰（S 2 S 2）-D-缬氨酸]（6）。羧甲基-L-半胱氨酸苄酯（1）与S-三苯甲基-L-半胱氨酰基-D-缬氨酸苄酯，随后除去保护基。二硫化物还原后，将游离的三肽Cys（CH 2 CO-Cys-D-Val）（Ib）用作异青霉素-N合成酶的底物，将其无细胞转化为6- [2-（（D- 2-氨基-2-羧乙基）硫）乙酰胺基]青霉酸（IIa）。
• Tailored Approaches towards the Synthesis of<scp>l</scp>-<i>S</i>-(Trifluoromethyl)cysteine- and<scp>l</scp>-Trifluoromethionine-Containing Peptides
  作者：Charlène Gadais、Nathalie Saraiva-Rosa、Evelyne Chelain、Julien Pytkowicz、Thierry Brigaud

  DOI：10.1002/ejoc.201601318

  日期：2017.1.10

  radical trifluoromethylation approach. The benzyl protecting group of these fluorinated amino acids could be conveniently removed by hydrogenolysis, which circumvented troublesome saponification reactions. For the first time, TfmCys was inserted into a peptide sequence by liquid- or solid-phase peptide synthesis. Finally, a late trifluoromethylation strategy with the use of Togni's reagent on disulfide-bridged

  在氟化的非经典氨基酸中，l-三氟甲硫氨酸 (TFM) 和 lS-（三氟甲基）半胱氨酸 (TFMCys)，甲硫氨酸和半胱氨酸的氟化类似物，由于它们能够局部增加肽的疏水性而受到特别关注。我们在此报告了通过使用廉价且用户友好的自由基三氟甲基化方法合成叔丁氧基羰基/苄基保护的 TFM 和 TFMCys。这些氟化氨基酸的苄基保护基团可以通过氢解方便地去除，从而避免了麻烦的皂化反应。首次通过液相或固相肽合成将 TFMCys 插入肽序列中。最后，使用 Togni' 的晚期三氟甲基化策略
• Stereoselective Synthesis of Orthogonally Protected α-Methylnorlanthionine
  作者：Alberto Avenoza、Jesús H. Busto、Gonzalo Jiménez-Osés、Jesús M. Peregrina

  DOI：10.1021/ol060993r

  日期：2006.6.1

  incorporated into cyclic peptide analogues of the ring C of lantibiotic nisin, we report here the stereoselective synthesis of the new (S,R)- and (R,R)-alpha-methylnorlanthionines (alpha-Me-nor-Lan). The orthogonally protected derivatives of these compounds have also been prepared. The key step in the synthesis of these bisamino acids was the S(N)2 opening reaction of the corresponding cyclic sulfamidates

  [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。