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. 2010 Jan 19;54(4):1404–1413. doi: 10.1128/AAC.01307-09

TABLE 1.

Antibacterial activities of lipopeptides and inhibition by bovine surfactant

Compounda Amino acid at position:
 MIC (μg/ml) for S. aureus 42b
2 3 5 6 8 9 11 12 13 − Surf + Surf (1%) Ratio (+/−)
Daptomycin d-Asn Asp Gly Orn d-Ala Asp d-Ser 3mGlu Kyn 0.5 64 128
CB-181,220 d-Asn Asp Gly Orn d-Ala Asp d-Ser 3mGlu Kyn 0.5 64 128
CB-182,098 d-Asn Asp Gly Orn d-Ala Asp d-Ser 3mGlu Trp 1 32 32
CB-182,107 d-Asn Asp Gly Orn d-Ala Asp d-Ser 3mGlu Ile 2 8 4
CB-182,106 d-Asn Asp Gly Orn d-Ala Asp d-Ser 3mGlu Val 4 8 2
CB-182,130 d-Asn Asp Gly Orn d-Ala Asp d-Ser Glu Kyn 8 16 2
CB-182,166 d-Asn Asp Gly Orn d-Ala Asp d-Ala 3mGlu Kyn 1 16 16
CB-182,290 d-Asn Asp Gly Orn d-Ala Asp d-Asn 3mGlu Kyn 1 16 16
CB-182,123 d-Asn Asp Gly Orn d-Ser Asp d-Ser 3mGlu Kyn 1 32 32
CB-182,296 d-Asn Asp Gly Orn d-Lys Asp d-Asn 3mGlu Kyn 1 32 32
A54145E d-Glu hAsn Sar Ala d-Lys moAsp d-Asn 3mGlu Ile 1 32 32
A54145D d-Glu hAsn Sar Ala d-Lys moAsp d-Asn Glu Ile 2 4 2
CB-182,548 d-Glu hAsn Sar Ala d-Lys moAsp d-Ala 3mGlu Ile 1 16 16
CB-182,332 d-Glu hAsn Sar Ala d-Lys moAsp d-Ser 3mGlu Ile 2 16 8
CB-182,571 d-Glu hAsn Sar Ala d-Ala moAsp d-Asn 3mGlu Ile 1 32 32
CB-182,549 d-Glu hAsn Sar Ala d-Ser moAsp d-Asn 3mGlu Ile 1 16 16
CB-182,510 d-Glu hAsn Sar Ala d-Asn moAsp d-Asn 3mGlu Ile 8 64 8
CB-182,363 d-Glu Asn Sar Ala d-Lys moAsp d-Asn 3mGlu Ile 2 16 8
CB-182,575 d-Asn hAsn Sar Ala d-Lys moAsp d-Asn 3mGlu Ile 2 4 2
CB-182,509 d-Glu hAsn Sar Ala d-Lys moAsp d-Ala Glu Ile 8 16 2
CB-182,336 d-Glu hAsn Sar Ala d-Lys moAsp d-Ser Glu Ile 64 128 2
CB-182,567 d-Glu hAsn Sar Ala d-Ala moAsp d-Asn Glu Ile 4 8 2
CB-182,532 d-Glu hAsn Sar Ala d-Ser moAsp d-Asn Glu Ile 8 8 1
CB-182,531 d-Glu hAsn Sar Ala d-Asn moAsp d-Asn Glu Ile 16 16 1
CB-182,444 d-Asn hAsn Sar Ala d-Lys moAsp d-Asn Glu Ile 8 8 1
CB-182,561 d-Asn Asp Sar Ala d-Lys moAsp d-Asn 3mGlu Ile 1 2 2
CB-182,560 d-Asn Asp Sar Ala d-Lys moAsp d-Asn Glu Ile 8 16 2
a

Daptomycin has a decanoyl side chain. All other compounds have anteiso-undecanoyl side chains. Amino acid substitutions are shown in boldface. The compounds related to daptomycin (CB-181,220 to CB-182,296) were generated in previous studies (32, 35, 36). A54145E and A54145D are natural lipopeptide factors produced by S. fradiae (8, 9); the latter is highly enriched by fermentation of an lptI mutant in a medium supplemented with l-Ile (Alexander et al., submitted).

b

− Surf, without surfactant; + Surf (1%), in the presence of 1% surfactant; ratio (+/−), ratio of the MIC in the presence of surfactant to the MIC in the absence of surfactant.