(R)-methyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)acetate | 26582-93-4

• 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: (R)-methyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)acetate
• 英文别名: N-tert-butyloxycarbonyl D-phenyl-alanine glycine methyl ester；methyl Boc-D-phenylalanylglycinate；^tert-Boc-D-Phe-Gly-OMe；Boc-D-Phe-Gly-OMe；N-[(1,1-Dimethylethoxy)carbonyl]-D-phenylalanylglycine methyl ester；methyl 2-[[(2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]amino]acetate
• CAS: 26582-93-4
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: KRYDBLGWCUNDCJ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-methyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)acetate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 Boc-D-phe-glyOH
  参考文献：
  名称：

  Aggregation propensity of amyloidogenic and elastomeric dipeptides constituents

  摘要：

  This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe-Gly and Pro-Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through various non-covalent interactions in the solid state which can be directly correlated with their fibrillation event in solution phase. Interestingly microscopic observations revealed that the amyloidogenic dipeptide constituents assembled into hollow tubular structures whereas the elastomeric dipeptide constituents assembled into the feather or sheet like structures. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.07.022
• 作为产物：
  描述：

  D-苯丙氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 13.0h， 生成 (R)-methyl 2-(2-(tert-butoxycarbonylamino)-3-phenylpropanamido)acetate
  参考文献：
  名称：

  Aggregation propensity of amyloidogenic and elastomeric dipeptides constituents

  摘要：

  This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe-Gly and Pro-Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through various non-covalent interactions in the solid state which can be directly correlated with their fibrillation event in solution phase. Interestingly microscopic observations revealed that the amyloidogenic dipeptide constituents assembled into hollow tubular structures whereas the elastomeric dipeptide constituents assembled into the feather or sheet like structures. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.07.022

文献信息

• Phosphorus pentoxide for amide and peptide bond formation with minimal by-products
  作者：Venkataramana Erapalapati、Umatai A. Hale、Nandita Madhavan

  DOI：10.1016/j.tetlet.2019.151311

  日期：2019.12

  Phosphorus pentoxide and DMAP are used for amide bond formation from carboxylic acids and amines. Dipeptides and amides have been synthesized using this reagent in 42-77% yields and >99% ees. The protocol is attractive as it occurs at ambient temperature, the formation of organic by-products is minimal and the reagent can be readily quenched using water. Furthermore, excellent enantioselectivities

  五氧化二磷和DMAP用于由羧酸和胺形成酰胺键。使用该试剂已合成了二肽和酰胺，产率为42-77％，ee大于99％。该方案具有吸引力，因为它在环境温度下发生，有机副产物的形成极少，并且试剂可以很容易地用水淬灭。此外，在不使用苛刻的三唑基添加剂的情况下，观察到优异的对映选择性。
• Retro peptides, antibodies thereto and their uses for vaccination and in vitro diagnosis
  申请人：Biomerieux S.A.

  公开号：US07122193B1

  公开（公告）日：2006-10-17

  The present invention relates to retro peptides, as well as antibodies thereto, and to their uses, chiefly in the field of preparation of pharmaceutical compositions, in particular vaccines, and for in vitro diagnosis of various pathologies.

  本发明涉及逆转肽，以及与之相关的抗体，以及它们的用途，主要用于制备药物组合物，特别是疫苗，并用于各种病理学的体外诊断。
• Toward the total synthesis of a lagunamide B analogue
  作者：Sudip Pal、Tushar Kanti Chakraborty

  DOI：10.1016/j.tetlet.2014.04.079

  日期：2014.6

  against Plasmodium falciparum and murine leukemia cell line (P388). Herein, a concise synthetic approach toward the total synthesis of a lagunamide B analogue is discussed. Macrolactonization, HWE-olefination, and modified Crimmin’s aldol are some of the key reactions featured in this synthesis.

  从新加坡发现的海洋蓝藻Lyngbya majuscule中分离出的Lagunamides对恶性疟原虫和鼠白血病细胞系（P388）表现出非常强的活性。在本文中，讨论了针对拉古酰胺B类似物的全合成的简明合成方法。宏观内酯化，HWE-烯烃化和改良的Crimmin's aldol是该合成过程中的一些关键反应。
• Aggregation propensity of amyloidogenic and elastomeric dipeptides constituents
  作者：Vikas Kumar、K. Vijaya Krishna、Shruti Khanna、Khashti Ballabh Joshi

  DOI：10.1016/j.tet.2016.07.022

  日期：2016.9

  This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe-Gly and Pro-Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through various non-covalent interactions in the solid state which can be directly correlated with their fibrillation event in solution phase. Interestingly microscopic observations revealed that the amyloidogenic dipeptide constituents assembled into hollow tubular structures whereas the elastomeric dipeptide constituents assembled into the feather or sheet like structures. (C) 2016 Elsevier Ltd. All rights reserved.