Colistin nonapeptide derivatives. III. Chemical synthesis and characterizations of n-fatty acyl monoaminoacyl derivatives of colistin nonapeptide.

  • Chihara S
  • Ito A
  • Yahata M
 et al. 
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To examine the antimicrobial activity of n-fatty acyl monoaminoacyl derivs. of colistin nonapeptide-HCl (CNP), 21 derivs. were synthesized and characterized on their chem. physicochem. and antimicrobial properties. Five α-amino acids, glycine [56-40-6], L-alanine [56-41-7], DL-aminobutyric acid [2835-81-6], DL-norvaline [760-78-1], and DL-norleucine [616-06-8], and 2 ω-amino acids, β-alanine [107-95-9] and γ-aminobutyric acid [56-12-2], were first acylated with each of 3 kinds of acid chloride, n-octanoyl [111-64-8], n-decanoyl [112-13-0], and n-dodecanoyl chloride [112-16-3], and then esterified with p-nitrophenol [100-02-7] prior to the coupling of those n-fatty acyl amino acids to the terminal threonine of CNP. The coupling reaction was carried out in an aq. solvent buffered at pH 5.0 without any protection of the γ-amino groups of CNP, as reported previously. All of the derivs., obtained as hydrochloride salts, were hygroscopic white amorphous powders, decompg. at 180 ∼230°. The antimicrobial spectra of the 15 n-fatty acyl α-aminoacyl CNPs against gram-neg. bacteria were narrower and the activities are less than those of the corresponding n-fatty acyl derivs. of CNP or colistin. Of n-fatty acyl ω-aminoacyl derivs., n-dodecanoyl β-alanyl-CNP showed unique antimicrobial spectrum against gram-neg. bacteria. Thus, the elongation of the peptide chain in the CNP mol. by a monoamino acid acylated with n-fatty acid resulted in the redn. of the antimicrobial activity except for a case of β-alanine; the activity seemed to depend on the kind of amino acid introduced. [on SciFinder(R)]

Author-supplied keywords

  • colistin nonapeptide deriv bactericide
  • peptide antibiotic deriv bactericide

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  • Shiro Chihara

  • Akira Ito

  • Masahiro Yahata

  • Takashi Tobita

  • Yasuo. Koyama

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