96) (+593 29) (+592 56) CIR 1222 57 1221 98 –  + Diacylglycerol (

96) (+593.29) (+592.56) CIR 1222.57 1221.98 –  + Diacylglycerol (C16/C19) (+831.36) (+830.77)      +N-acyl (C16)       LppX CSS…EIR 2964.46 – - CSS…EIR 3515.33 3514.94 3514.94  + Diacylglycerol (C16/C16) (+550.87) (+550.48) (+550.48) CSS…EIR 3557.42 – 3556.96  + Diacylglycerol (C16/C19) (+592.96)   (+592.50) CSS…EIR 3719.66 mTOR inhibitor – 3719.00  + Diacylglycerol

(C16/C19) (+755.20)   (+754.54)  +Hexose       CSS…EIR 3795.82 3795.21 –  + Diacylglycerol (C16/C19) (+831.36) (+830.75)    + N-acyl (C16)       CSS…EIR 3881.90 – 3881.06  + Diacylglycerol (C16/C19) (+917.44)   (+916.60)  + 2 Hexoses       CSS…EIR 3958.06 3957.28 –  + Diacylglycerol (C16/C19) (+993.60) (+992.82)    + N-acyl (C16)        + Hexose       CSS…EIR 4120.30 4119.45 –  + Diacylglycerol (C16/C19) (+1155.84) (+1154.99)    + N-acyl (C16)          + 2 Hexoses       Peptides correspond to the N-terminal AspN-digested/tryptic peptides of LprF, LpqH, LpqL and LppX upon cleavage of the signal peptide by LspA. Mass differences to the corresponding unmodified peptide (bold number) due to modifications are given in parentheses. Observed modifications are: diacylglycerol with C16 fatty acid and C16 fatty acid (+550.87 Da). Diacylglycerol with C16 fatty acid and tuberculostearic acid (C19:0) (+592.96 Da), plus one hexose (+162.24 Da, Σ = 755.20 Da)

AZD5153 solubility dmso or two hexoses (+324.48 Da, Σ = 917.44). Diacylglycerol with C16 fatty acid and C19:0 fatty acid (+592.96 Da) plus N-acyl with C16 fatty acid (+238.40 Da, Σ = 831.36), N-acyl with C16 fatty acid plus one hexose (+162.24 Da, Σ = 993.6 Da) or two hexoses (+324.48 Da, Σ = 1155.84 Da). Or diacylglycerol with C16 fatty acid and C19:0 fatty acid (+592.96 Da) plus N-acyl with C19:0 fatty acid and hexose (+280.49 Da +162.24 Σ = 1035.69). The modifications we estimated (-)-p-Bromotetramisole Oxalate from the [M+H]+ signals in the MS spectrum were confirmed by MS/MS fragmentation and thereby information about the linkage of the modification was obtained. The structures of the di- or triacylated N-terminal tryptic or AspN-digested peptides from LprF, LpqH, LpqL and LppX were investigated by MS/MS. All eliminations found in MS/MS of lipoproteins isolated

from the parental strain are summarized in Table 2. Table 2 Comparison of experimentally determined eliminations from N-terminal AspN digested/tryptic peptides of LprF, LpqH, LpqL and LppX in the MALDI-TOF/TOF spectra of BCG parental and Δ lnt mutant strain with theoretically calculated eliminations Modification Eliminated fragment Calculated mass of eliminated fragment [ Da ] Experimentally determined mass of eliminated fragment [ Da ] Parental strain Δlnt LprF LpqH LpqL LppX LprF LpqH LpqL LppX       C16/C19 C16 C16/C19 C19 C16/C19 C16 C16/C19 C16   C16/C16 C16/C19 C16/C16 C16/C18 C16/C19 C16/C19   O-linked palmitoyl (C16) Palmitic acid 256.24 256.5 – 256.3 256.3 n.d. * – - 256.2 256.1 256.3 256.3 n.d. * O-linked oleyl (C18) Oleic acid 282.24 – - – - n.d. * – - – 282.4 – - n.d. * O-linked tuberculostearyl (C19) Tuberculostearic acid 298.

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