N-tert-butoxycarbonyl-L-tryptophan-L-aspartate dimethylester | 910239-37-1

• 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-tert-butoxycarbonyl-L-tryptophan-L-aspartate dimethylester
• 英文别名: Boc-Trp-Asp(OMe)-OMe；dimethyl (2S)-2-[[(2S)-3-(1H-indol-3-yl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]butanedioate
• CAS: 910239-37-1
• 化学式: C₂₂H₂₉N₃O₇
• 分子量: 447.488
• InChiKey: OPDNRWCFLCNMIA-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-tryptophan-L-aspartate dimethylester 在 盐酸 、 TEA 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of modified fragments of fibrinogen and their effect on the activity of proteolytic enzymes

  摘要：

  New analogues of the Gly-Pro-Arg and Arg-Gly-Asp fragments of fibrinogen were synthesized: Gly-Pro-Arg-Pro (1), Gly-Pro-Arg-Pro-Met-We (11), Gly-Pro-Arg-Pro-Phe (111), Gly-Pro-Arg-Pro-Asp (IV), Gly-Pro-Arg-Pro-Glu (V), and Arg-Asn-Trp-Asp (VI). Their effect on the activity of proteases of various types was studied with the method of lysis of fibrin plates. All the peptides were found to inhibit plasmin activity (by 60-85%) and the gamma-subunit of nerve growth factor (by 55-93%). Tetrapeptide (VI) proved to be an effective inhibitor of tissue activator of plasminogen and the 7-subunit of nerve growth factor (by 96 and 93%, respectively). The peptides exerted practically no effect on the activity of urokinase and moderately inhibited the activity of streptokinase [(III), IV), and (VI)], papain [(I), (II), IV), and (VI)], subtilisin [(V) and (VI)], (x-chymotrypsin [(III), (V), and VI)], and Bacillus subtilis metalloprotease (VI). They inhibit trypsin [except for (1) and (111)] when applied on fibrin plates at a concentration of I X 10(-2) M, while, at the concentration of I X 10(-3) M, (1) and (11) induced an increase in proteolytic activity by 35 and 47%, respectively.

  DOI：

  10.1134/s106816200602004x
• 作为产物：
  描述：

  L-天冬氨酸二甲酯盐酸盐 、 N-叔丁氧羰基-L-色氨酸 在 sodium carbonate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以85%的产率得到N-tert-butoxycarbonyl-L-tryptophan-L-aspartate dimethylester
  参考文献：
  名称：

  含色氨酸肽的光化学选择性烷基化

  摘要：

  我们报告了一种用于含色氨酸 (Trp) 肽的化学选择性自由基功能化的光化学方法。该方法利用色氨酸单元和吡啶盐之间产生的电子供体-受体复合物的光活性。用弱光 (390 nm) 照射会在目标 Trp 氨基酸旁边产生自由基中间体，促进邻近驱动的自由基功能化。该协议对 Trp 残基比其他氨基酸具有高化学选择性，并且可以耐受生物相容性条件。

  DOI：

  10.1021/acs.orglett.0c03735

文献信息

• Tryptophan-containing dipeptide derivatives as potent PPARγ antagonists: Design, synthesis, biological evaluation, and molecular modeling
  作者：Guanghui Deng、Zhiguo Liu、Fei Ye、Xiaomin Luo、Weiliang Zhu、Xu Shen、Hong Liu、Hualiang Jiang

  DOI：10.1016/j.ejmech.2008.01.032

  日期：2008.12

  The discovery of peroxisome proliferator-activated receptor gamma (PPAR gamma) antagonists (also termed "selective PPAR gamma modulators, SPPAR gamma M") is now of a great interest in the treatment of diabetes and obesity. The structure of compound la (G3335, Fig. 1), a novel class of PPAR gamma antagonist, is entirely different from that of other reported PPAR gamma antagonists. A series of 35 novel analogues (1b-1, 9a-d, 13a-t) were designed, synthesized and evaluated against the agonistic effects exerted by rosiglitazone. These results indicated that most functional groups of la were conserved, and six new compounds (1b, 1c, and 9a-d) exhibited strong PPAR gamma antagonistic activities (IC50 values of 5.2-25.8 mu M) against 10 mu M rosiglitazone in the promotion of the PPAR gamma-LBD-CBP (ligand-binding domain and cAMP-response-element binding protein) interaction as investigated by yeast two-hybrid technology based assay. Molecular modeling studies for compounds 1a-d, 1h, 9c-d, and 13a were also presented. (C) 2008 Elsevier Masson SAS. All rights reserved.