N-(tert-Butoxycarbonyl)-L-tyrosyl p-nitrobenzyl ester | 92264-95-4

• 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: N-(tert-Butoxycarbonyl)-L-tyrosyl p-nitrobenzyl ester
• 英文别名: Boc-Tyr-ONB；(4-nitrophenyl)methyl (2S)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 92264-95-4
• 化学式: C₂₁H₂₄N₂O₇
• 分子量: 416.431
• InChiKey: GMDNMQPTZZXDTE-SFHVURJKSA-N

物化性质

• 沸点：
  604.1±55.0 °C(Predicted)
• 密度：
  1.281±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(tert-Butoxycarbonyl)-L-tyrosyl p-nitrobenzyl ester 在 palladium on activated charcoal N-甲基吗啉 、 四氮唑 、 sodium dithionite 、 氢气 、 间氯过氧苯甲酸 、 氯甲酸异丁酯 作用下， 以 溶剂黄146 为溶剂， -20.0~50.0 ℃ 、101.33 kPa 条件下， 反应 3.97h， 生成 H-Tyr(PO3H2)-Leu-Gly-OH TFA
  参考文献：
  名称：

  Synthesis of O-phosphotyrosine-containing peptides. 1. Synthesis of PTyr-Leu-Gly via benzyl phosphate protection

  摘要：

  DOI：

  10.1021/jo00268a047
• 作为产物：
  描述：

  Boc-L-酪氨酸 、 对硝基溴化苄 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 生成 N-(tert-Butoxycarbonyl)-L-tyrosyl p-nitrobenzyl ester
  参考文献：
  名称：

  两种合成磷酸酪氨酸肽的液体二次电离质谱表征

  摘要：

  合成这些 en phase solide etude des schemas de fragmentation de Val-X-Phe et de Arg-X-Val-Phe (X=O-phosphonotyrosyl)

  DOI：

  10.1021/ja00252a007

文献信息

• Liquid secondary ionization mass spectrometric characterization of two synthetic phosphotyrosine-containing peptides
  作者：Bradford W. Gibson、Arnold M. Falick、A. L. Burlingame、Lazslo Nadasdi、Nguyen Ann Cac、George L. Kenyon

  DOI：10.1021/ja00252a007

  日期：1987.9

  Synthese en phase solide et etude des schemas de fragmentation de Val-X-Phe et de Arg-X-Val-Phe (X=O-phosphonotyrosyl)

  合成这些 en phase solide etude des schemas de fragmentation de Val-X-Phe et de Arg-X-Val-Phe (X=O-phosphonotyrosyl)
• Tetrapeptidehydrazide derivatives
  申请人：Takeda Chemical Industries, Ltd

  公开号：US04277394A1

  公开（公告）日：1981-07-07

  Novel tetrapeptidehydrazide derivatives, inclusive of a pharmacologically acceptable acid addition salt thereof, which has the general formula (I): ##STR1## [wherein R.sub.1 is hydrogen or lower alkyl; R.sub.2 is hydrogen or the side chain of a D-.alpha.-amino acid; R.sub.3 is hydrogen or lower alkyl; R.sub.4 is hydrogen, or a saturated or unsaturated and straight or branched lower aliphatic acyl group which may optionally be substituted by hydroxy, amino, lower alkoxy, halogen, oxo, lower alkylthio or lower alkylthiooxide], are useful as analgesics.

  具有以下一般式（I）的新型四肽酸酐衍生物，包括其药学上可接受的酸盐： ##STR1## [其中R.sub.1是氢或低级烷基；R.sub.2是氢或D-.alpha.-氨基酸的侧链；R.sub.3是氢或低级烷基；R.sub.4是氢，或饱和或不饱和的直链或支链低级脂肪酰基，该基团可以选择性地被羟基，氨基，低级烷氧基，卤素，氧代，低级烷硫基或低级烷硫氧化物取代]，可用作镇痛剂。
• Synthesis of Prodrug Candidates:  Conjugates of Amino Acid with Nucleoside Boranophosphate
  作者：Ping Li、Barbara Ramsay Shaw

  DOI：10.1021/ol025832b

  日期：2002.6.1

  [GRAPHIC]Preparation of antiviral and anticancer prodrug candidates, P-tyrosinyl(P-O)-5'-P-nucleosidyl boranophosphates, is described. One-pot synthesis via a phosphoramidite method resulted in the title compounds with good yields. The P-boranophosphate diastereomers were separated by RP-HPLC, and their structures were confirmed by H-1 and P-31 NMR spectroscopy and MS analysis.
• Synthesis of protected derivatives of O-phosphotyrosine incorporation in a heptapeptide
  作者：R.M. Valerio、P.F. Alewood、R.B. Johns、B.E. Kemp

  DOI：10.1016/s0040-4039(01)81243-0

  日期：1984.1
• Synthesis of a Phosphotyrosine-Containing Peptide Fragment of the Regulatory Domain of pp60c-src
  作者：Eung-Seok Lee、Mark Cushman

  DOI：10.1021/jo00087a025

  日期：1994.4

  t-Boc-Tyr(PO(3)Me(2))-OH (4) was ulitized in the synthesis of PheThrSerThrGluProGlnTyr(PO3H2)-GlnProGlyGluAsnLeu (1), a phosphotyrosine-containing peptide fragment of the regulatory domain of pp60(c-src). The protected amino acid 4 was employed during the synthesis of PheThrSerThrGluProGlnTyr(PO(3)Me(2))GlnProGlyGluAsnLeu (5), during which problems involving incomplete incorporation of the Tyr(PO(3)Me(2)) residue, as well as partial demethylation of the dimethylphosphono group and dephoshhorylation during peptide synthesis, were encountered. In addition, an acid-catalyzed backbone rearrangement was encountered involving migration of the phenylalanine acyl group from the nitrogen to the hydroxyl group of the adjacent threonine residue during the deprotection of the phosphate group of 5 with a mixture of trifluoromethanesulfonic acid, trifluoroacetic acid, dimethyl sulfide, and m-cresol (10:50:30:10).