N-[芴甲氧羰基]-O-(三苯基甲基)-D-丝氨酸 | 212688-51-2

• 物质功能分类: 生物化工 - 生化试剂 - 氨基酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: N-[芴甲氧羰基]-O-(三苯基甲基)-D-丝氨酸
• 中文别名: Fmoc-O-三苯甲基-D-丝氨酸；FMOC-D-丝氨酸(TRT)
• 英文名称: Fmoc-D-Ser(Trt)-OH
• 英文别名: (2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-trityloxypropanoic acid
• CAS: 212688-51-2
• 化学式: C₃₇H₃₁NO₅
• 分子量: 569.657
• InChiKey: UCARTONYOJORBQ-UUWRZZSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  43
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• WGK Germany：
  2
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H320,H335

反应信息

• 作为反应物：
  描述：

  N-[芴甲氧羰基]-O-(三苯基甲基)-D-丝氨酸 、 N-methyl-L-phenylalanine methyl ester 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以97%的产率得到Fmoc-D-Ser(Trt)-L-MePhe-OMe
  参考文献：
  名称：

  通过布朗斯台德酸促进的酰基N-甲基咪唑鎓阳离子的生成来合成N-甲基化的肽。

  摘要：

  牢固的酰胺键形成的发展仍然是N-甲基化肽合成的关键方面。在这项研究中，我们从等量的氨基酸中高收率合成了各种二肽，而没有严重的消旋作用。高反应性的N-甲基咪唑鎓阳离子原位生成以加速酰胺化反应。成功的关键是加入强力的布朗斯台德酸。与常规酰胺化的结果相比，开发的酰胺化使得能够在较短的时间内以较高的产率合成大体积的肽。另外，可以通过使用微流反应器或常规烧瓶来进行酰胺化。天然存在的大体积N-甲基化肽，蝶酰胺I-IV的首次全合成。根据实验结果和理论计算，

  DOI：

  10.1002/anie.202002106

文献信息

• [EN] CONJUGATES OF TACROLIMUS, THEIR COMPOSITIONS, AND THEIR USES<br/>[FR] CONJUGUÉS DE TACROLIMUS, LEURS COMPOSITIONS ET LEURS UTILISATIONS
  申请人：THE ADMINISTRATORS OF THE TULANE EDUCATIONAL FUND

  公开号：WO2017165607A1

  公开（公告）日：2017-09-28

  Some embodiments of the invention include inventive compounds (e.g., compounds of Formula (I)) including but not limited to conjugates comprising FK-506 and ascomycin. Other embodiments include compositions (e.g., pharmaceutical compositions) comprising the inventive compound. Still other embodiments of the invention include compositions for treating, for example, certain diseases using the inventive compounds. Some embodiments include methods of using the inventive compound (e.g., in compositions or in pharmaceutical compositions) for administering and treating. Further embodiments include methods for making the inventive compound. Additional embodiments of the invention are also discussed herein.

  本发明的某些实施例包括创新化合物（例如，公式（I）的化合物），包括但不限于包含FK-506和ascomycin的缀合物。其他实施例包括由创新化合物组成的组合物（例如，药物组合物）。本发明的进一步实施例包括用于治疗某些疾病的组合物，例如，使用创新化合物。一些实施例包括使用创新化合物的方法（例如，在组合物中或药物组合物中）用于给药和治疗。进一步的实施例包括制造创新化合物的方法。本发明还讨论了其他的实施例。
• Rapid, Structure-Based Exploration of Pipecolic Acid Amides as Novel Selective Antagonists of the FK506-Binding Protein 51
  作者：Steffen Gaali、Xixi Feng、Andreas Hähle、Claudia Sippel、Andreas Bracher、Felix Hausch

  DOI：10.1021/acs.jmedchem.5b01355

  日期：2016.3.24

  However, drug-like parameters for these ligands remained unfavorable. In the present study, we replaced the potentially labile pipecolic ester group of previous FKBP51 ligands by various low molecular weight amides. This resulted in the first series of pipecolic acid amides, which had much lower molecular weights without affecting FKBP51 selectivity. We discovered a geminally substituted cyclopentyl

  FK506结合蛋白51（FKBP51）是压力激素受体的关键调节剂，并且是与压力相关的疾病的既定危险因素。FKBP51的药物开发受到结构相似但功能相反的同系物FKBP52的破坏。FKBP51和FKBP52之间的高选择性可以通过稳定最近发现的FKBP51有利构象的配体来实现。然而，这些配体的药物样参数仍然是不利的。在本研究中，我们用各种低分子量酰胺取代了以前的FKBP51配体的潜在不稳定的胡椒酸酯基。这产生了第一系列的胡椒酸酰胺，其具有低得多的分子量而不影响FKBP51的选择性。
• Oxathiocoraline: Lessons to be Learned from the Synthesis of Complex<i>N</i>-Methylated Depsipeptides
  作者：Núria Bayó-Puxan、Judit Tulla-Puche、Fernando Albericio

  DOI：10.1002/ejoc.200900259

  日期：2009.6

  Investigations into the synthesis of oxathiocoraline, a bicyclic depsipeptide with C2 symmetry, revealed a number of unexpected side-reactions that could not be circumvented by classical or standard means. This cyclodepsipeptide has a large number of N-methyl amino acids coexisting with two ester bonds and also shows a branched structure; these features hinder its synthesis. In addition, complexity

  对 oxathiocoraline（一种具有 C2 对称性的双环缩酚肽）合成的研究揭示了许多传统或标准方法无法避免的意外副反应。这种环缩肽含有大量的N-甲基氨基酸并以两个酯键共存，也呈现支链结构；这些特征阻碍了它的合成。此外，由于存在大量非市售半胱氨酸和杂环部分，复杂性进一步增加。在这里，我们描述了在尝试合成环缩肽时应解决的一般问题，例如防止或最小化二酮哌嗪形成、β-消除和氧化副产物的策略。最佳设计包括合适的固体支持物，
• An Entirely Solid Phase Peptide Synthesis-Based Strategy for Synthesis of Gelatinase Biosynthesis-Activating Pheromone (GBAP) Analogue Libraries: Investigating the Structure–Activity Relationships of the <i>Enterococcus faecalis</i> Quorum Sensing Signal
  作者：Dominic N. McBrayer、Brooke K. Gantman、Crissey D. Cameron、Yftah Tal-Gan

  DOI：10.1021/acs.orglett.7b01444

  日期：2017.6.16

  The development of an entirely solid-phase peptide synthesis (SPPS)-based synthesis of the quorum sensing signal gelatinase biosynthesis-activating pheromone (GBAP) from Enterococcus faecalis is reported. The method was used to prepare three libraries of analogues to investigate the structure–activity relationships (SARs) of the GBAP signal. The SAR studies revealed new characteristics of the GBAP

  报告了粪肠球菌的群体感应信号明胶酶生物合成激活信息素（GBAP）的基于完全固相肽合成（SPPS）的合成技术的发展。该方法用于制备三个类似物库，以研究GBAP信号的结构-活性关系（SAR）。SAR研究揭示了GBAP信号的新特征，并揭示了迄今为止已知的粪肠球菌中最有效的群体感应激活剂。
• Enhanced Epimerization of Glycosylated Amino Acids During Solid-Phase Peptide Synthesis
  作者：Yalong Zhang、Saddam M. Muthana、David Farnsworth、Olaf Ludek、Kristie Adams、Joseph J. Barchi、Jeffrey C. Gildersleeve

  DOI：10.1021/ja212188r

  日期：2012.4.11

  Glycopeptides are extremely useful for basic research and clinical applications, but access to structurally defined glycopeptides is limited by the difficulties in synthesizing this class of compounds. In this study, we demonstrate that many common peptide coupling conditions used to prepare O-linked glycopeptides result in substantial amounts of epimerization at the a position. In fact, epimerization resulted in up to 80% of the non-natural epimer, indicating that it can be the major product in some reactions. Through a series of mechanistic studies, we demonstrate that the enhanced epimerization relative to nonglycosylated amino acids is due to a combination of factors, including a faster rate of epimerization, an energetic preference for the unnatural epimer over the natural epimer, and a slower overall rate of peptide coupling. In addition, we demonstrate that use of 2,4,6-trimethylpyridine (TMP) as the base in peptide couplings produces glycopeptides with high efficiency and low epimerization. The information and improved reaction conditions will facilitate the preparation of glycopeptides as therapeutic compounds and vaccine antigens.