N,O-bis-allyloxycarbonyl-L-tyrosine | 104669-68-3

• 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,O-bis-allyloxycarbonyl-L-tyrosine
• 英文别名: N,O-Bis-allyloxycarbonyl-L-tyrosin；o,n-Dicarboallyloxy-l-tyrosine；(2S)-2-(prop-2-enoxycarbonylamino)-3-(4-prop-2-enoxycarbonyloxyphenyl)propanoic acid
• CAS: 104669-68-3
• 化学式: C₁₇H₁₉NO₇
• 分子量: 349.34
• InChiKey: YXOQXDQLDXZJAO-AWEZNQCLSA-N

物化性质

• 熔点：
  105 °C(Solv: ethanol, 50% (64-17-5))
• 沸点：
  529.4±50.0 °C(Predicted)
• 密度：
  1.250±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,O-bis-allyloxycarbonyl-L-tyrosine 在 bis-triphenylphosphine-palladium(II) chloride 三正丁基氢锡 作用下， 以 二氯甲烷 为溶剂， 以95%的产率得到L-酪氨酸
  参考文献：
  名称：

  钯催化氢化三丁基锡的反应。氨基酸的烯丙基和烯丙氧基羰基衍生物的选择性非常温和的脱保护。

  摘要：

  烯丙基（All）和烯丙氧基羰基（Alloc）氨基酸衍生物通过Bu 3 SnH以高选择性的方式通过钯催化的氢化锡烷基水解进行脱保护。苄基和苄氧羰基在这些条件下是稳定的。此外，烯丙基和Alloc基团似乎与叔丁基和叔丁氧羰基保护基团正交。

  DOI：

  10.1016/s0040-4039(00)84530-x
• 作为产物：
  描述：

  L-酪氨酸 、 氯甲酸烯丙酯 以 sodium hydroxide 为溶剂， 以O,N-dicarboallyloxy-L-tyrosine is obtained in 89% yield (Litt. 91%) as a crystalline derivative的产率得到N,O-bis-allyloxycarbonyl-L-tyrosine
  参考文献：
  名称：

  CD4 mimic peptides and their uses

  摘要：

  本文披露了一种孤立的肽，包括序列（I）：TPA-Asn-Leu-His-Phe-Cys-Gln-Leu-Xaaa-Cys-Lys-Ser-Leu-Gly-Leu-Leu-Gly-Arg-Cys-Xaab-Xaac-Xaad-Xaae-Cys-Ala-Cys-Val-NH2，其中：TPA代表硫代丙酸；Xaaa代表Arg，Lys；Xaab代表Ala，Arg；Xaac代表D-氨基酸；Xaad代表Thr，Ser，Asn；Xaae代表苯丙氨酸或具有结构式（II）的苯丙氨酸衍生物，其中A不存在或代表S，O，NH或CH2，B不存在或代表C1至C6支链或直链烷基，R代表C3至C6烷基，杂基烷基，环烷基，杂环烷基，环烯基，环杂环烯基，芳基或杂芳基，并且本文还揭示了使用该肽制造抗HIV治疗或疫苗组合物的用途。

  公开号：

  US08354498B2

文献信息

• CD4 MIMIC PEPTIDES AND THEIR USES
  申请人：Vita Claudio

  公开号：US20090285798A1

  公开（公告）日：2009-11-19

  An isolated peptide comprising the sequence (I): TPA-Asn-Leu-His-Phe-Cys-Gln-Leu-Xaa a -Cys-Lys-Ser-Leu-Gly-Leu-Leu-Gly-Arg-Cys-Xaa b -Xaa c -Xaa d -Xaa e -Cys-Ala-Cys-Val-NH 2 , wherein: TPA represents thiopropionic acid; Xaa a represents Arg, Lys; Xaa b represents Ala, Arg; Xaa c represents a D-amino acid; Xaa d represents Thr, Ser, Asn; Xaa e represents phenylalanine or a phenylalanine derivative having the structure (II), where A is absent or represents S, O, NH or CH 2 , B is absent or represents a C 1 to C 6 branched or straight-chain alkyl, and R represents a C 3 to C 6 alkyl, heteroalkyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, cycloheterocyloalkenyl, aryl, or heteroaryl, and the use of the peptide for manufacturing anti-HIV therapeutic or vaccine compositions are disclosed herein.

  本文披露了一种孤立的肽，包括序列(I): TPA-Asn-Leu-His-Phe-Cys-Gln-Leu-Xaaa-Cys-Lys-Ser-Leu-Gly-Leu-Leu-Gly-Arg-Cys-Xaab-Xaac-Xaad-Xaae-Cys-Ala-Cys-Val-NH2，其中：TPA代表硫代丙酸；Xaaarepresents Arg，Lys；Xaabrepresents Ala，Arg；Xaacrepresents a D-氨基酸；Xaadrepresents Thr，Ser，Asn；Xaaerepresents苯丙氨酸或具有结构(II)的苯丙氨酸衍生物，其中A不存在或代表S，O，NH或CH2，B不存在或代表C1到C6的支链或直链烷基，R代表C3到C6烷基，杂基烷基，环烷基，杂环烷基，环烯基，环杂环烯基，芳基或杂芳基。本文还披露了利用该肽制造抗HIV治疗或疫苗组合物的用途。
• Specific fragmentation of thioxo peptides facilitates the assignment of the thioxylated amino acid
  作者：Thomas Pfeifer、Angelika Schierhorn、Rudolf Friedemann、Mario Jakob、Robert Frank、Mike Schutkowski、Gunter Fischer

  DOI：10.1002/(sici)1096-9888(199711)32:10<1064::aid-jms560>3.0.co;2-7

  日期：1997.11

  Low-energy collision-induced dissociation (CID) product ion spectra of a series of singly protonated thioxo peptides produced by electrospray ionization (ESI) were obtained by triple-quadrupole tandem mass spectrometry. The principal feature of the spectra is a preferential cleavage of the peptide bond succeeding the thioxo peptide moiety. Thus this method provides the possibility of assigning the position of the thioxylated amino acid in oligopeptides resulting from the thioxylation procedure with Lawesson's or a related reagent. At low collision energy, dominant B ions and/or complementary Y '' ions are observed. Higher collision energy yields internal ions that consist of two adjacent amino acids encompassing the thioxo peptide bond. The formation of these internal ions and the elimination of CO from them give evidence for the position of the thioxylated amino acid. There are strong indications of a stabilization of the B and internal ions through the formation of a thiazolone. Fragment ions resulting from the cleavage of the thioxo peptide bond are either completely absent or of very low intensity. (C) by John Wiley & Sons, Ltd.No. of Figures:10 No. of Tables:0 No. of Refs:41.
• The Use of Benzylsulfonyl Chloride in Peptide Syntheses^1,2
  作者：H. Bayard Milne、Chi-Hsieh Peng

  DOI：10.1021/ja01560a036

  日期：1957.2
• Selective cleavage of the allyl and (allyloxy)carbonyl groups through palladium-catalyzed hydrostannolysis with tributyltin hydride. Application to the selective protection-deprotection of amino acid derivatives and in peptide synthesis
  作者：O. Dangles、F. Guibe、G. Balavoine、S. Lavielle、A. Marquet

  DOI：10.1021/jo00231a027

  日期：1987.10
• Amino Acid Derivatives. I. Carboallyloxy Derivatives of α-Amino Acids^1,2
  作者：Carl M. Stevens、Ronald Watanabe

  DOI：10.1021/ja01158a020

  日期：1950.2