N-(三苯基甲基)-L-丝氨酸与三乙胺的化合物 | 111061-44-0

• 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-(三苯基甲基)-L-丝氨酸与三乙胺的化合物
• 中文别名: 三苯甲基-L-丝氨酸三乙胺复合物(1:1)
• 英文名称: N-Trityl-L-Serin-Triethylammonium-Salz
• 英文别名: triethylammonium N-trityl-L-serine；triethylammonium tritylserine；Trt-L-Ser-OH triethylammonium salt；(2S)-3-hydroxy-2-(tritylamino)propanoate;triethylazanium
• CAS: 111061-44-0
• 化学式: C₆H₁₅N*C₂₂H₂₁NO₃
• 分子量: 448.605
• InChiKey: HHNPFPJZXOFNOZ-BDQAORGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(三苯基甲基)-L-丝氨酸与三乙胺的化合物 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 为溶剂， 反应 13.58h， 生成 N-benzyl-1-trityl-L-aziridine-2-carboxamide
  参考文献：
  名称：

  硫醇与含氮丙啶-2-羧酸肽的位点选择性偶联

  摘要：

  描述了含氮丙啶-2-羧酸的肽与硫醇在溶液和固体支持物上的合成和会聚位点选择性偶联。FmocAzyOH 在这种能力下的合成和使用证明了 Azy 部分在多步 Fmoc 固相肽合成 (SPPS) 中的有效掺入和耐受性，以及通过高度区域选择性碱基进行溶液和珠上连接的能力。促进氮丙啶开环过程。

  DOI：

  10.1021/ja046793x

文献信息

• Aziridine-2-carboxylic Acid-Containing Peptides:  Application to Solution- and Solid-Phase Convergent Site-Selective Peptide Modification
  作者：Danica P. Galonić、Nathan D. Ide、Wilfred A. van der Donk、David Y. Gin

  DOI：10.1021/ja050304r

  日期：2005.5.25

  The development of a method for site- and stereoselective peptide modification using aziridine2-carboxylic acid-containing peptides is described. A solid-phase peptide synthesis methodology that allows for the rapid generation of peptides incorporating the aziridine residue has been developed. The unique electrophilic nature of this nonproteinogenic amino acid allows for site-selective conjugation with various thiol nucleophiles, such as anomeric carbohydrate thiols, farnesyl thiol, and biochemical tags, both in solution and on solid support. This strategy, combined with native chemical ligation, provides convergent and rapid access to complex thioglycoconjugates.
• Barlos, Kleomenis; Mamos, Petros; Papaioannou, Dionysios, Liebigs Annalen der Chemie, 1987, p. 1025 - 1030
  作者：Barlos, Kleomenis、Mamos, Petros、Papaioannou, Dionysios、Patrianakou, Stella、Sanida, Chariklia、Schaefer, Wolfram

  DOI：——

  日期：——
• Ring-Opening of Aziridine-2-Carboxamides with Carbohydrate C1-<i>O</i>-Nucleophiles. Stereoselective Preparation of α- and β-<i>O</i>-Glycosyl Serine Conjugates
  作者：Daniel A. Ryan、David Y. Gin

  DOI：10.1021/ja804589j

  日期：2008.11.19

  The stereoselective formation of the alpha-GalNAc-Ser linkage via the ring opening of aziridine-2-carboxamides with pyranose C1-O-nucleophiles is described. The process is tolerant to the native C2-NHAc group, can be modulated to provide either the alpha- or beta-glycoside through judicious choice of solvent and metal counterion, and is amenable to other classes of O-glycosyl-Ser constructs such as the B-GlcNAc-Ser and alpha-Man-Ser linkages. This coupling reaction also led to the development of the o-allylbenzyl (ABn) moiety as a new C-terminus carboxyl protective group, which allows for the use of novel methods for N- and C-terminus extension of amino acids following carbohydrate conjugation.
• BARLOS, KLEOMENIS;MAMOS, PETROS;PAPAIOANNOU, DIONYSIOS;PARTIANAKOU, STELL+, LIEBIGS ANN. CHEM.,(1987) N 12, 1025-1030
  作者：BARLOS, KLEOMENIS、MAMOS, PETROS、PAPAIOANNOU, DIONYSIOS、PARTIANAKOU, STELL+

  DOI：——

  日期：——
• AMINO ACID HAVING FUNCTIONAL GROUP CAPABLE OF INTERMOLECULAR HYDROGEN BONDING, PEPTIDE COMPOUND CONTAINING SAME AND METHOD FOR PRODUCTION THEREOF
  申请人：Chugai Seiyaku Kabushiki Kaisha

  公开号：US20230096766A1

  公开（公告）日：2023-03-30

  It has been found that the membrane permeability of peptide compounds can be improved by making at least one of amino acids constituting the peptide compound be an amino acid having a side chain capable of forming an intramolecular hydrogen bond.