H-Arg(NO2)-Ala-OBzl | 47557-07-3

• 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: H-Arg(NO2)-Ala-OBzl
• 英文别名: Arg(NO2)-Ala-OCH2-C6H5；benzyl (2S)-2-[[(2S)-2-amino-5-[[amino(nitramido)methylidene]amino]pentanoyl]amino]propanoate
• CAS: 47557-07-3
• 化学式: C₁₆H₂₄N₆O₅
• 分子量: 380.404
• InChiKey: IECAOUHBQPNLKF-AAEUAGOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  178
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  H-Arg(NO2)-Ala-OBzl 在 palladium on activated charcoal N-乙基吗啉 、 1,4-环己二烯 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 PhO-CH2CO-Arg(NO2)-Ala
  参考文献：
  名称：

  Synthesis of Analogs of D-Ala--D-Ala as Potential Inhibitors of Bacterial Cell Wall Biosynthesis.

  摘要：

  The syntheses of the L,L- and D,D-stereoisomers of N- phenoxyacetyl -X-alanine in which X = Ser, Ala( beta Cl ) or Arg, are described. The antibacterial activity of these peptides and some of their synthetic intermediates has been examined. Four of the intermediates in which X = Ala( beta Cl ) and Arg(NO2), which possess C-terminal benzyl ester groups, were active against viridans streptococci and Streptococcus agalactiae. The D,D-enantiomers were more active than the corresponding L,L-isomers. None of the compounds were active against beta-lactamase producing bacteria or acted as beta-lactamase inhibitors.

  DOI：

  10.3891/acta.chem.scand.38b-0005
• 作为产物：
  描述：

  Boc-Arg(NO2)-Ala-OBzl 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 0.01h， 以82%的产率得到H-Arg(NO2)-Ala-OBzl
  参考文献：
  名称：

  MW‐Enhanced High‐Speed Deprotection of Boc Group Usingp‐TsOH and Concommitant Formation ofN‐Me‐Amino Acid Benzyl Esterp‐TsOH Salts

  摘要：

  A high-speed, complete deprotection of Boc group from Boc amino acids and protected peptide esters employing p-TsOH in toluene under microwave irradiation is found to be complete in 30 s. The deprotection can be carried out in methanol and acetonitrile also. Under the present conditions, C-peptide benzyl esters and O-benzyl ethers have been found to be stable. This has permitted us to carry out the synthesis of [Leu] enkephalin employing the Boc/Bzl-group strategy. Further more, it has been found that both N-alpha-Fmoc and N-alpha-Z groups are completely stable. The present conditions can be extended for the concomitant removal of the Boc group and the formation of C-benzyl amino acid esters as well. This has been utilized for the synthesis of N-Me amino acid benzyl esters starting from Boc-N-Me amino acids in a single step.

  DOI：

  10.1081/scc-200063953

文献信息

• Über Peptidsynthesen, XXIX 4. Mitteilung über Glukagon-Teilsequenzen. Synthese der Glukagon-Teilsequenzen 12–19 und 1–19
  作者：Eberhard Schröder

  DOI：10.1002/jlac.19656810133

  日期：1965.1.22

  Die Glukagonsequenz 12–19 wurde als Nϵ-BOC-Lys-Tyr-Leu-Asp(NH2)-Ser-Arg-Arg-Ala-OH·2CH3COOH·4H2O aus Nα-Cbo-Nϵ-BOC-Lys-Tyr-N3 und H-Leu-Asp(NH2)-Ser-(NO2)Arg-(NO2)Arg-Ala-OCH2C6H5·CF3COOH durch anschließende katalytische Hydrierung des Octapeptids synthetisiert. Umsetzung der Sequenz 12–19 mit der bereits beschriebenen N-terminalen Sequenz 1–11 lieferte das Glukagon-Teilstück 1–19 als BOC-His-(O-tBu

  死Glukagonsequenz 12-19 wurde ALS Ñ ε-BOC-赖氨酸酪氨酸-亮氨酸-天冬氨酸（NH 2）-Ser基-Arg-Arg-Ala-OH·2CH 3 COOH·4H 2 öAUS Ñ α -Cbo- Ñ ε- BOC-Lys-Tyr-N 3和H-Leu-Asp（NH 2）-Ser-（NO 2）Arg-（NO 2）Arg-Ala-OCH 2 C 6 H 5 ·CF 3 COOH八肽合成。塞昆茨河畔乌姆塞宗（Umsetzung der Sequenz）12-19米特尔·贝希里本（N-terminalen Sequenz）1-11卢塞贡·达斯·卢卡贡·泰尔斯泰克（Lyferte dasGlukagon-Teilstück）1-19岁BOC-His-（O -tBu）Ser-Glu（NH 2）-Gly-Thr-Phe-Thr-Ser-Asp（NH 2）-Tyr-Ser-（N
• 390. Syntheses of peptidyl-nucleotidates including L-arginyl-L-alanyl-L-arginyl-L-alanyl uridine-5? phosphate
  作者：G. Harris、I. C. MacWilliam

  DOI：10.1039/jr9610002053

  日期：——
• MW‐Enhanced High‐Speed Deprotection of Boc Group Using<i>p</i>‐TsOH and Concommitant Formation of<i>N</i>‐Me‐Amino Acid Benzyl Ester<i>p</i>‐TsOH Salts
  作者：Vommina V. Suresh Babu、Basanagoud S. Patil、Ganga‐Ramu Vasanthakumar

  DOI：10.1081/scc-200063953

  日期：2005.7

  A high-speed, complete deprotection of Boc group from Boc amino acids and protected peptide esters employing p-TsOH in toluene under microwave irradiation is found to be complete in 30 s. The deprotection can be carried out in methanol and acetonitrile also. Under the present conditions, C-peptide benzyl esters and O-benzyl ethers have been found to be stable. This has permitted us to carry out the synthesis of [Leu] enkephalin employing the Boc/Bzl-group strategy. Further more, it has been found that both N-alpha-Fmoc and N-alpha-Z groups are completely stable. The present conditions can be extended for the concomitant removal of the Boc group and the formation of C-benzyl amino acid esters as well. This has been utilized for the synthesis of N-Me amino acid benzyl esters starting from Boc-N-Me amino acids in a single step.
• Synthesis of Analogs of D-Ala--D-Ala as Potential Inhibitors of Bacterial Cell Wall Biosynthesis.
  作者：Erik A. Hagen、Tom Bergan、Arne J. Aasen、Lester A. Mitscher、Daniel T. W. Chu

  DOI：10.3891/acta.chem.scand.38b-0005

  日期：——

  The syntheses of the L,L- and D,D-stereoisomers of N- phenoxyacetyl -X-alanine in which X = Ser, Ala( beta Cl ) or Arg, are described. The antibacterial activity of these peptides and some of their synthetic intermediates has been examined. Four of the intermediates in which X = Ala( beta Cl ) and Arg(NO2), which possess C-terminal benzyl ester groups, were active against viridans streptococci and Streptococcus agalactiae. The D,D-enantiomers were more active than the corresponding L,L-isomers. None of the compounds were active against beta-lactamase producing bacteria or acted as beta-lactamase inhibitors.