Daptomycin and lipopeptide antibiotics generated by combinatorial biosynthesis. Adapted from Baltz 2014.172 A schematic representation of Daptomycin with numbered amino acids is available in Fig. 6A.
| Compound | Amino acid at position | Side chain | S. aureus MIC (ug mL−1) | ||||||||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 2 | 3 | 5 | 6 | 8 | 9 | 11 | 12 | 13 | −Surf | +Surf | Ratio (±) | ||
| Daptomycin | D-Asn | Asp | Gly | Orn | D-Ala | Asp | D-Ser | 3mGlu | Kyn | N-decanoyl | 0.5 | 64 | 128 |
| CB-182,107 | D-Asn | Asp | Gly | Orn | D-Ala | Asp | D-Ser | 3mGlu | Ile | Anteiso-undecanoyl | 2 | 8 | 4 |
| CB-182,106 | D-Asn | Asp | Gly | Orn | D-Ala | Asp | D-Ser | 3mGlu | Val | Anteiso-undecanoyl | 4 | 8 | 2 |
| A54145E | D-Glu | hAsn | Sar | Ala | D-Lys | moAsp | D-Asn | 3mGlu | Ile | Anteiso-undecanoyl | 1 | 32 | 32 |
| A54145D | D-Glu | hAsn | Sar | Ala | D-Lys | moAsp | D-Asn | Glu | Ile | Anteiso-undecanoyl | 2 | 4 | 2 |
| CB-183,296 | D-Glu | hAsn | Sar | Ala | D-Lys | moAsp | D-Asn | Glu | Kyn | Anteiso-undecanoyl | 1 | 2 | 2 |
| CB-182,390 | D-Glu | Asn | Sar | Ala | D-Lys | Asp | D-Asn | 3mGlu | Ile | Anteiso-undecanoyl | 2 | 2 | 1 |
| CB-182,561 | D-Asn | Asp | Sar | Ala | D-Lys | moAsp | D-Asn | 3mGlu | Ile | Anteiso-undecanoyl | 1 | 2 | 2 |