Derivatization of Aminoglycoside Antibiotics with Tris(2,6-dimethoxyphenyl)carbenium Ion

A P Topolyan; M A Belyaeva; E E Bykov; P V Coodan; E A Rogozhin; D A Strizhevskaya; O M Ivanova; A V Ustinov; I V Mikhura; I A Prokhorenko; V A Korshun; A A Formanovsky

Derivatization of Aminoglycoside Antibiotics with Tris(2,6-dimethoxyphenyl)carbenium Ion

Acta Naturae. 2016 Jul-Sep;8(3):128-135.

Authors

Affiliations

¹ Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Moscow, 117997, Russia.
² Gause Institute of New Antibiotics, Moscow, 119021, Russia.
³ Research Institute of Nutrition, Moscow, 109240, Russia.
⁴ Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Moscow, 117997, Russia ; Gause Institute of New Antibiotics, Moscow, 119021, Russia.

PMID: 27795853
PMCID: PMC5081711

Abstract

Detection of aminoglycoside antibiotics by MS or HPLC is complicated, because a) carbohydrate molecules have low ionization ability in comparison with other organic molecules (particularly in MALDI-MS), and b) the lack of aromatics and/or amide bonds in the molecules makes common HPLC UV-detectors useless. Here, we report on the application of a previously developed method for amine derivatization with tris(2,6- dimethoxyphenyl)carbenium ion to selective modification of aminoglycoside antibiotics. Only amino groups bound to primary carbons get modified. The attached aromatic residue carries a permanent positive charge. This makes it easy to detect aminoglycoside antibiotics by MS-methods and HPLC, both as individual compounds and in mixtures.

Keywords: HPLC; aminoglycoside antibiotics; mass-spectrometry; trityl cation.