TABLE 1.
Chemical structures of the naturally occurring polymyxins
Reprinted by permission from the Springer Nature: Springer, Adv Exp Med Biol, History, chemistry and antibacterial spectrum, Velkov T. et al. Copyright © 2019.
| Polymyxin | Fatty Acyl Group | Position 3 | Position 6 | Position 7 | Position 10 |
|---|---|---|---|---|---|
| A1 | (S)-6-Methyloctanoyl | d-Dab | d-Leu | l-Thr | l-Thr |
| A2 | 6-Methylheptanoyl | d-Dab | d-Leu | l-Thr | l-Thr |
| B1 | (S)-6-Methyloctanoyl | l-Dab | d-Phe | l-Leu | l-Thr |
| B2 | 6-Methylheptanoyl | l-Dab | d-Phe | l-Leu | l-Thr |
| B3 | Octanoyl | l-Dab | d-Phe | l-Leu | l-Thr |
| B4 | Heptanoyl | l-Dab | d-Phe | l-Leu | l-Thr |
| B5 | Nonanoyl | l-Dab | d-Phe | l-Leu | l-Thr |
| B6 | 3-Hydroxy-6-methyloctanoyla | l-Dab | d-Phe | l-Leu | l-Thr |
| B1-Ile | (S)-6-Methyloctanoyl | l-Dab | d-Phe | l-Ile | l-Thr |
| B2-Ile | 6-Methylheptanoyl | l-Dab | d-Phe | l-Ile | l-Thr |
| Dab3-B1 | (S)-6-Methyloctanoyl | d-Dab | d-Phe | l-Leu | l-Thr |
| Dab3-B2 | 6-Methylheptanoyl | d-Dab | d-Phe | l-Leu | l-Thr |
| C1b | 6-Methyloctanoyla | l/d-Dab | d-Phe | l-Thr | l-Thr |
| C2b | 6-Methylheptanoyl | l/d-Dab | d-Phe | l-Thr | l-Thr |
| D1 | (S)-6-Methyloctanoyl | d-Ser | d-Leu | l-Thr | l-Thr |
| D2 | 6-Methylheptanoyl | d-Ser | d-Leu | l-Thr | l-Thr |
| E1 (Colistin A) | (S)-6-Methyloctanoyl | l-Dab | d-Leu | l-Leu | l-Thr |
| E2 (Colistin B) | 6-Methylheptanoyl | l-Dab | d-Leu | l-Leu | l-Thr |
| E3 | Octanoyl | l-Dab | d-Leu | l-Leu | l-Thr |
| E4 | Heptanoyl | l-Dab | d-Leu | l-Leu | l-Thr |
| E7 | 7-Methyloctanoyl | l-Dab | d-Leu | l-Leu | l-Thr |
| E1-Ile | (S)-6-Methyloctanoyl | l-Dab | d-Leu | l-Ile | l-Thr |
| E1-Val | (S)-6-Methyloctanoyl | l-Dab | d-Leu | l-Val | l-Thr |
| E1-Nva | (S)-6-Methyloctanoyl | l-Dab | d-Leu | l-Nva | l-Thr |
| E2-Ile | 6-Methylheptanoyl | l-Dab | d-Leu | l-Ile | l-Thr |
| E2-Val | 6-Methylheptanoyl | l-Dab | d-Leu | l-Val | l-Thr |
| E8-Ile | 7-Methylnonanoyl | l-Dab | d-Leu | l-Ile | l-Thr |
| Fb | 6-Methyloctanoylc | l/d-Dab | d-Leu/d-Ile | l-Leu/l-Ile/l-Ser | l-Leu/l-Ile/l-Ser |
| Fb | 6-Methylheptanoyl | l/d-Dab | d-Leu/d-Ile | l-Leu/l-Ile/l-Ser | l-Leu/l-Ile/l-Ser |
| Fb | Octanoyl | l/d-Dab | d-Leu/d-Ile | l-Leu/l-Ile/l-Ser | l-Leu/l-Ile/l-Ser |
| M1 (Mattacin) | (S)-6-Methyloctanoyl | d-Dab | d-Leu | l-Thr | l-Thr |
| M2 (Mattacin) | 6-Methylheptanoyl | d-Dab | d-Leu | l-Thr | l-Thr |
| P1 | (S)-6-Methyloctanoyl | d-Dab | d-Phe | l-Thr | l-Thr |
| P2 | 6-Methylheptanoyl | d-Dab | d-Phe | l-Thr | l-Thr |
| S1 | 6-Methyloctanoylc | d-Ser | d-Phe | l-Thr | l-Thr |
| T1 | 6-Methyloctanoylc | l-Dab | d-Phe | l-Leu | l-Leu |
| T2 | 6-Methylheptanoyl | l-Dab | d-Phe | l-Leu | l-Leu |
Stereochemistry at C3 and C6 not confirmed.
Position of amino acid residues is speculative.
Stereochemistry at C6 not confirmed.