Boc-Arg(NO2)-Ala-OBzl | 2132-52-7

• 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: Boc-Arg(NO2)-Ala-OBzl
• 英文别名: tert.-Butoxycarbonyl-nitro-L-arginyl-L-alanin-benzylester；benzyl (2S)-2-[[(2S)-5-[[amino(nitramido)methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoyl]amino]propanoate
• CAS: 2132-52-7
• 化学式: C₂₁H₃₂N₆O₇
• 分子量: 480.521
• InChiKey: ULNZJFGJRXKQLR-HOCLYGCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  34
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  190
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  N'-硝基-L-精氨酸 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 Boc-Arg(NO2)-Ala-OBzl
  参考文献：
  名称：

  Wuensch,E.; Zwick,A., Chemische Berichte, 1964, vol. 97, p. 3312 - 3316

  摘要：

  DOI：

文献信息

• 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.