Abstract
The acylation of unprotected vancomycin or eremomycin with activated esters of Nα-protected amino acids or Nα-alkyl-Nα-Fmoc-amino acids is directed selectively to the amino group of the disaccharide branch (N′) and after Fmoc-group removal leads to the corresponding N′-α-aminoacyl derivatives. A series of N′-α-aminoacyl and N′-α-(Nα-alkylamino)acyl derivatives of eremomycin and vancomycin containing hydrophobic moieties has been synthesized. The structures of all derivatives were confirmed by Electrospray Ionization mass-spectral (ESI MS) analysis, and by chemical degradation methods. Position of the introduced N′-α-aminoacyl- and N-(Nα-alkylamino)acyl groups were determined after Edman degradation and acidic hydrolysis.The structures of the synthesized starting reagents (Nα-alkylamino acids or Nα-alkyl-Nα-Fmocamino acids) were confirmed by NMR-spectra data. In general, N′-(N-alkylglycyl)-derivatives were more active than the corresponding N′-α-(Nα-alkylamino)acylated derivatives containing other amino acids (L-Lys, L-Met, L-Orn, L- and D-Ala, L- and D-Phe and benzyl-O-L-Tyr).
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Preobrazhenskaya, M., Olsufyeva, E., Miroshnikova, O. et al. N′-(α-Aminoacyl)- and N′-α-(Nα-Alkylamino)acyl Derivatives of Vancomycin and Eremomycin. J Antibiot 60, 235–244 (2007). https://doi.org/10.1038/ja.2007.28
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DOI: https://doi.org/10.1038/ja.2007.28
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