N-叔丁氧羰基-L-天冬氨酸 1-(9H-芴-9-基甲基)酯 | 129046-87-3

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 天冬氨酸类衍生物
• 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
• 中文名称: N-叔丁氧羰基-L-天冬氨酸 1-(9H-芴-9-基甲基)酯
• 中文别名: N-叔丁氧羰基-L-天冬氨酸1-(9H-芴-9-基甲基)酯；N-叔丁氧羰基-l-天冬氨酸1-(9h-芴-9-甲基)酯
• 英文名称: fluoren-9-ylmethyl N-tert-butyloxycarbonyl-L-aspartate
• 英文别名: Boc-L-Asp-OFm；Boc-L-Asp(OH)-OFm；Boc-Asp-Ofm；(3S)-4-(9H-fluoren-9-ylmethoxy)-3-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid
• CAS: 129046-87-3
• 化学式: C₂₃H₂₅NO₆
• 分子量: 411.455
• InChiKey: RMRKPGGMJKNMSK-IBGZPJMESA-N

物化性质

• 熔点：
  138-142℃
• 沸点：
  617.4±55.0 °C(Predicted)
• 密度：
  1.251

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

制备方法与用途

简介

N-叔丁氧羰基-L-天冬氨酸 1-(9H-芴-9-基甲基)酯为氨基酸衍生物，可用于生物化工领域。

反应信息

• 作为反应物：
  描述：

  N-叔丁氧羰基-L-天冬氨酸 1-(9H-芴-9-基甲基)酯 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 fluoren-9-ylmethyl L-aspartate
  参考文献：
  名称：

  An unexpected product from attempted reductive etherification of a silyl alcohol with an aldehyde

  摘要：

  Reductive etherification, using BiBr3/Et3SiH, between two modified amino acids, one with a silyl alcohol side chain and one with an aldehyde side chain, gave, not the desired bis-amino acid, but a tetrahydrooxazine, in good yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.163
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 N,N-二甲氨基-2-氯丙烷盐酸盐 、 sodium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 52.0h， 生成 N-叔丁氧羰基-L-天冬氨酸 1-(9H-芴-9-基甲基)酯
  参考文献：
  名称：

  An unexpected product from attempted reductive etherification of a silyl alcohol with an aldehyde

  摘要：

  Reductive etherification, using BiBr3/Et3SiH, between two modified amino acids, one with a silyl alcohol side chain and one with an aldehyde side chain, gave, not the desired bis-amino acid, but a tetrahydrooxazine, in good yield. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.163

文献信息

• Synthesis of a Glycosylated Peptide Thioester by the Boc Strategy and Its Application to Segment Condensation
  作者：Eiichiro HAGINOYA、Hironobu HOJO、Yuko NAKAHARA、Yoshiaki NAKAHARA、Kazuki NABESHIMA、Bryan P. TOOLE、Yasushi WATANABE

  DOI：10.1271/bbb.50621

  日期：2006.6.23

  The synthesis of a chitobiosylated peptide thioester by the t-butoxycarbonyl (Boc) strategy is demonstrated. Boc-Asn carrying benzyl-protected chitobiose was introduced during application of the Boc mode solid-phase method. HF treatment of the resulting protected peptide resin gave the desired chitobiosylated peptide thioester. This thioester was used to prepare the peptide sequence derived from extracellular matrix metalloproteinase inducers (emmprin) (34-94), (34-118) and (22-118) by the thioester segment condensation method. The conformation of these glycopeptides is characterized by circular dichroism (CD) spectral measurement.

  本文展示了通过叔丁氧羰基（Boc）策略合成壳寡糖化肽硫酯的过程。在应用 Boc 模式固相方法时，引入了携带苄基保护壳寡糖的 Boc-Asn。对得到的受保护肽树脂进行 HF 处理，可得到所需的壳寡糖化肽硫酯。利用这种硫酯通过硫酯段缩合法制备了源自细胞外基质金属蛋白酶诱导剂（emmprin）（34-94）、（34-118）和（22-118）的肽序列。这些糖肽的构象是通过圆二色性（CD）光谱测量确定的。
• An efficient approach for monosulfide bridge formation in solid-phase peptide synthesis
  作者：Pietro Campiglia、Isabel Gomez-Monterrey、Luigi Longobardo、Teresa Lama、Ettore Novellino、Paolo Grieco

  DOI：10.1016/j.tetlet.2003.12.036

  日期：2004.2

  for the synthesis of cyclic peptides containing unnatural thioether side-chain bridges, based on the use of (2S)-9-fluorenylmethyl-2-[(tert-butoxycarbonyl)amino]-4-iodobutanoate and its homologue 5-iodopentanoate, derived from Boc-l-Asp-OFm and Boc-l-Glu-OFm, respectively, is reported. The synthesis was performed by a tandem combination of solid-phase peptide synthesis and microwave-assisted cyclization

  基于使用（2 S）-9-芴基甲基-2-[（叔丁氧基羰基）氨基] -4-碘代丁酸酯及其同系物5-的合成含非天然硫醚侧链桥的环肽的有效方法报道了分别衍生自Boc-1-Asp-OFm和Boc-1-Glu-OFm的碘戊酸酯。通过固相肽合成和微波辅助环化策略的串联组合进行合成。
• Novel thiol- and thioether-containing amino acids: cystathionine and homocysteine families
  作者：Luigi Longobardo、Nunzia Cecere、Marina DellaGreca、Ivan de Paola

  DOI：10.1007/s00726-012-1352-5

  日期：2013.2

  Natural l-homocysteine and l,l-cystathionine, along with a series of unnatural analogues, have been prepared from l-aspartic and l-glutamic acid. Manipulation of the protected derivatives provided omega-iodoamino acids, which were used in thioalkylation reactions of sulfur nucleophiles, such as the ester of l-cysteine and potassium thioacetate.
• US6008058A
  申请人：——

  公开号：US6008058A

  公开（公告）日：1999-12-28