N-(9-芴甲氧羰基)-L-丝氨酸苯甲酰甲酯 | 125760-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 中文名称: N-(9-芴甲氧羰基)-L-丝氨酸苯甲酰甲酯
• 英文名称: N-Fmoc serine phenacyl ester
• 英文别名: Fmoc-Ser-O-Pha；N-(9-Fluorenylmethoxycarbonyl)-L-serine Phenacyl Ester；phenacyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxypropanoate
• CAS: 125760-26-1
• 化学式: C₂₆H₂₃NO₆
• 分子量: 445.472
• InChiKey: PYOVUIPZMRWLQC-QHCPKHFHSA-N

物化性质

• 密度：
  1.304

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(9-芴甲氧羰基)-L-丝氨酸苯甲酰甲酯 在 四氮唑 、 溶剂黄146 、 间氯过氧苯甲酸 、 锌 作用下， 生成 Fmoc-丝氨酸磷酸苄酯
  参考文献：
  名称：

  An Efficient Procedure for Solid-Phase Synthesis of Phosphopeptides by the Fmoc Strategy

  摘要：

  Fmoc 模式固相方法被成功地应用于建立合成磷酸肽的实用程序。Fmoc 磷酸丝氨酸及其磷酸单苄酯衍生物被作为合成多肽的起始原料之一进行了研究。与前者相比，后者在产物的产率和纯度方面取得了更好的结果。

  DOI：

  10.1246/cl.1994.1099
• 作为产物：
  描述：

  Fmoc-L-丝氨酸 、 2-溴苯乙酮 在 caesium carbonate 作用下， 生成 N-(9-芴甲氧羰基)-L-丝氨酸苯甲酰甲酯
  参考文献：
  名称：

  An Efficient Procedure for Solid-Phase Synthesis of Phosphopeptides by the Fmoc Strategy

  摘要：

  Fmoc 模式固相方法被成功地应用于建立合成磷酸肽的实用程序。Fmoc 磷酸丝氨酸及其磷酸单苄酯衍生物被作为合成多肽的起始原料之一进行了研究。与前者相比，后者在产物的产率和纯度方面取得了更好的结果。

  DOI：

  10.1246/cl.1994.1099

文献信息

• βGal(1–3)GalNAc block donor for the synthesis of TF and α Sialy(2–6)TF as glycopeptide building blocks
  作者：Dongxu Qiu、Sham S. Gandhi、R.Rao Koganty

  DOI：10.1016/0040-4039(95)02229-5

  日期：1996.1

  with peracetylated galactose is found to be an excellent donor for the synthesis of Thomsen-Freidenreich (TF) family of antigens. These may serve further as building blocks for the synthesis of mucin derived glycopeptides and as intermediates for further extention to trisaccharides such as sialyl-TF and 6-O-βGlcNAc-TF(core 2). TF and Sialylated TF are widely regarded as tumor associated and are being

  发现在3位用过乙酰化的半乳糖保护的4,6-苄叉基保护的N-乙酰半乳糖胺β-糖基化是合成Thomsen-Freidenreich（TF）家族抗原的极好供体。这些可以进一步用作合成粘蛋白衍生的糖肽的基础，并用作进一步延伸至三糖如唾液酸-TF和6-O-βGlcNAc-TF（核心2）的中间体。TF和唾液酸化的TF被广泛认为是与肿瘤相关的，并且正在被研究作为抗原用于上皮来源的癌症的免疫治疗。
• 1-Methyl 1′-cyclopropylmethyl (MCPM) as an anomeric protecting group
  作者：Siu Hong Yu、Dennis M. Whitfield

  DOI：10.1016/j.tet.2011.05.133

  日期：2011.8

  oligosaccharide as a building block with most of its protecting groups exchanged to protecting groups whose cleavage and other manipulations are highly compatible with the functional groups of complex aglycones. For such an approach the reducing end sugar of the building bloc must be protected with a cleavable protecting group during the oligosaccharide synthesis. We demonstrate that the acid labile 1-methyl

  制备复杂寡糖的糖缀合物的实用方法是将寡糖作为结构单元，将其大多数保护基交换为保护基，该保护基的裂解和其他操作与复杂糖苷配基的官能团高度相容。对于这种方法，必须在寡糖合成过程中用可裂解的保护基团保护建筑集团的还原端糖。我们证明了酸不稳定的1-甲基1'-环丙基甲基（MCPM）可以有效地用于此目的。制备三糖糖脂和二糖糖氨基酸。通过结合NMR NOE测量，DFT分子建模和Noyori催化剂催化的不对称还原反应，可以确定一个关键受体中MCPM的绝对手性。
• An Efficient Procedure for Solid-Phase Synthesis of Phosphopeptides by the Fmoc Strategy
  作者：Tateaki Wakamiya、Kunio Saruta、Jun-ichi Yasuoka、Shoichi Kusumoto

  DOI：10.1246/cl.1994.1099

  日期：1994.6

  The Fmoc-mode solid-phase method was successfully applied to establish a practical procedure for the synthesis of phosphopeptides. Both Fmoc-phosphoserine with free phosphoric moiety and its monobenzyl phosphate derivative were examined as one of starting materials for the synthesis of peptides. The employment of the latter gave better result in respects of the yield and purity of the product than that obtained with the former.

  Fmoc 模式固相方法被成功地应用于建立合成磷酸肽的实用程序。Fmoc 磷酸丝氨酸及其磷酸单苄酯衍生物被作为合成多肽的起始原料之一进行了研究。与前者相比，后者在产物的产率和纯度方面取得了更好的结果。
• Application of t-butyldimethylsilyl ethers of serine, threonine and tyrosine in peptide syntheshsis
  作者：Peter M. Fischer

  DOI：10.1016/s0040-4039(00)60836-5

  日期：——

  The utility of Tbdms (t-butyldimethylsilyl) ethers, prepared conveniently in a one-pot procedure from N(alpha)-Fmoc (9-fluorenylmethoxycarbonyl) and N(alpha)-Z (benzyloxycarbonyl) hydroxyamino acids, is demonstrated: peptide bond formation and esterification to 4-alkoxybenzylalcohol resin are achieved readily with these derivatives. The lability of the Tbdms ethers to various reagents enables selective deprotection of the hydroxyl side-chains after peptide chain assembly, desirable, e.g., for phosphorylation or glycosilation.
• Synthesis of gold nanoparticles bearing the Thomsen–Friedenreich disaccharide: a new multivalent presentation of an important tumor antigen
  作者：Sergei A. Svarovsky、Zoltan Szekely、Joseph J. Barchi

  DOI：10.1016/j.tetasy.2004.12.003

  日期：2005.1

  Herein we describe the synthesis gold nanoshells encapsulated with up to 90 units of the Thomsen-Friedenreich (TF) tumor-associated carbohydrate antigen (TACA) disaccharide (Galbeta1-3GaINAc-alpha-O-Ser/Thr) as well as the assembly of a suitably linked designer glycopeptide as a precursor to similar multivalent presentations on gold. The TF-coated nanoparticles are highly stable, water soluble, and easily handled. Improvements in the linker technology used to attach the disaccharide to the particles led to a robust multivalent platform for the presentation of this important carbohydrate. The antigen retains all recognition characteristics while displayed on this template as shown by several in vitro assays. This area of research could lead to the development of novel therapeutic agents that inhibit protein-carbohydrate interactions. Published by Elsevier Ltd.