deaminoteicoplanin pseudoaglycon | 117226-74-1

• 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: deaminoteicoplanin pseudoaglycon
• CAS: 117226-74-1
• 化学式: C₆₆H₅₇Cl₂N₇O₂₃
• 分子量: 1387.12
• InChiKey: USYUDJQGQMEUSB-PJLICBPBSA-N

反应信息

• 作为产物：
  描述：

  (1S,2R,19R,22S,34S,37R,40R,52S)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-amino-5,15-dichloro-26,31,44,47,49,64-hexahydroxy-21,35,38,54,56,59-hexaoxo-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[38.14.2.23,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid 在 sodium hydroxide 、 hydroxylamine-O-sulfonic acid 作用下， 以 水 、 乙腈 为溶剂， 以0.2 g的产率得到deaminoteicoplanin pseudoaglycon
  参考文献：
  名称：

  Deaminoteicoplanin and its derivatives. Synthesis, antibacterial activity, and binding strength to Ac-D-Ala-D-Ala

  摘要：

  Teicoplanin and its acid hydrolysis products were deaminated with hydroxylamine-O-sulfonic acid (HOS). A few amides of these deaminoteicoplanins were also prepared. The loss of the terminal amino group reduces in vitro activity against staphylococcal and streptococcal bacteria to one-half to one-third, while binding strength to Ac-D-Ala-D-Ala, measured by differential UV spectroscopy, is reduced to one-tenth that of teicoplanin. The in vitro activity is further reduced by the presence of serum, and this is attributable to the increased lipophilicity and total negative charge of the deamino compounds. Comparison of UV spectra of deaminoteicoplanins with those of parent compounds made it possible to single out the most acid phenol group of teicoplanin aglycon (OH-4; pK = 8.2).

  DOI：

  10.1021/jm00122a007