N-tert-butoxycarbonyl-L-phenylalanine-L-aspartate dibenzyllester | 145435-30-9

• 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: N-tert-butoxycarbonyl-L-phenylalanine-L-aspartate dibenzyllester
• 英文别名: BocNH-L-Ala-L-Asp(OBn)-OBn；Boc-Phe-Asp(OBn)-OBn；dibenzyl (2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]butanedioate
• CAS: 145435-30-9
• 化学式: C₃₂H₃₆N₂O₇
• 分子量: 560.647
• InChiKey: PFWZZYPJILOLOB-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  120
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-phenylalanine-L-aspartate dibenzyllester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以100%的产率得到dibenzyl (2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]butanedioate;hydrochloride
  参考文献：
  名称：

  抗病毒肽抗生素泛霉素的全合成

  摘要：

  一种适应性强的方法：Feglymycin（见结构）及其对映异构体的第一个高度收敛的立体选择性合成是基于重复肽片段的偶联。在整个合成过程中使用弱碱性条件抑制了敏感的芳基甘氨酸单元的差向异构化。Feglymycin具有强大的抗HIV活性以及对金黄色葡萄球菌的有效（先前被确认为弱）抗菌活性。

  DOI：

  10.1002/anie.200804130
• 作为产物：
  描述：

  4-羟基苯硫酚 在 sodium hydroxide 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 80.0h， 生成 N-tert-butoxycarbonyl-L-phenylalanine-L-aspartate dibenzyllester
  参考文献：
  名称：

  Peptide Synthesis in Aqueous Solution. V. Properties and Reactivities of (p-Hydroxyphenyl)benzylmethylsulfonium Salts for Direct Benzyl Esterification ofN-Acylpeptides

  摘要：

  制备了一些（对羟基苯基）苄基甲基硫盐。这些化合物生成了苄基阳离子，并且不仅将N-酰基氨基酸，还将N-酰基肽转化为其相应的苄基酯，而没有引起消旋化。

  DOI：

  10.1246/bcsj.69.1099

文献信息

• Total Synthesis of the Antiviral Peptide Antibiotic Feglymycin
  作者：Frank Dettner、Anne Hänchen、Dominique Schols、Luigi Toti、Antje Nußer、Roderich D. Süssmuth

  DOI：10.1002/anie.200804130

  日期：2009.2.23

  An adaptable approach: The first highly convergent stereoselective synthesis of feglymycin (see structure) and its enantiomer is based on the coupling of repeating peptide fragments. The use of weakly basic conditions throughout the synthesis suppressed the epimerization of sensitive aryl glycine units. Feglymycin has strong anti‐HIV activity as well as potent (previously identified as weak) antibacterial

  一种适应性强的方法：Feglymycin（见结构）及其对映异构体的第一个高度收敛的立体选择性合成是基于重复肽片段的偶联。在整个合成过程中使用弱碱性条件抑制了敏感的芳基甘氨酸单元的差向异构化。Feglymycin具有强大的抗HIV活性以及对金黄色葡萄球菌的有效（先前被确认为弱）抗菌活性。
• 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.
• Peptide Synthesis in Aqueous Solution. V. Properties and Reactivities of (<i>p</i>-Hydroxyphenyl)benzylmethylsulfonium Salts for Direct Benzyl Esterification of<i>N</i>-Acylpeptides
  作者：Takashi Nakata、Masaru Nakatani、Masatoshi Takahashi、Jiro Okai、Yoshiaki Kawaoka、Katsushige Kouge、Hideo Okai

  DOI：10.1246/bcsj.69.1099

  日期：1996.4

  Some (p-hydroxyphenyl)benzylmethylsulfonium salts were prepared. These compounds generated a benzyl cation and converted not only N-acylamino acids but also N-acylpeptides into their corresponding benzyl esters without causing the racemization.

  制备了一些（对羟基苯基）苄基甲基硫盐。这些化合物生成了苄基阳离子，并且不仅将N-酰基氨基酸，还将N-酰基肽转化为其相应的苄基酯，而没有引起消旋化。
• Alanine Scan of the Peptide Antibiotic Feglymycin: Assessment of Amino Acid Side Chains Contributing to Antimicrobial Activity
  作者：Anne Hänchen、Saskia Rausch、Benjamin Landmann、Luigi Toti、Antje Nusser、Roderich D. Süssmuth

  DOI：10.1002/cbic.201300032

  日期：2013.3.18

  antibiotic feglymycin was performed by solution‐phase peptide synthesis to assess the significance of individual amino acid side chains for its biological activity. Antibacterial activity against Staphylococcus aureus and the inhibition of enzymes MurA and MurC depend on different amino acids.

  单模扫描：通过溶液相肽合成对肽抗生素海藻霉素进行丙氨酸扫描，以评估单个氨基酸侧链对其生物学活性的重要性。对金黄色葡萄球菌的抗菌活性和对酶MurA和MurC的抑制取决于不同的氨基酸。