Highly’Active’Antibacterial’Ferrocenoylated’or ... · ! 1! SC%EDG%06%2014%001822!!...
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1 SCEDG062014001822 Supporting Information for Highly Active Antibacterial Ferrocenoylated or Ruthenocenoylated ArgTrp Peptides can be Discovered by an LtoD Substitution Scan by H. Bauke Albada, Pascal Prochnow, Sandra Bobersky, Julia E. Bandow, Nils MetzlerNolte* Contents: MALDITOF MS data of the FcC(O) and RcC(O)WRWRWNH 2 peptides (Table S1) p. 2 HPLCtraces of the RcC(O)WRWRWNH 2 peptides p. 3–13 Electronic Supplementary Material (ESI) for Chemical Science. This journal is © The Royal Society of Chemistry 2014
Transcript of Highly’Active’Antibacterial’Ferrocenoylated’or ... · ! 1! SC%EDG%06%2014%001822!!...
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SC-‐EDG-‐06-‐2014-‐001822
Supporting Information
for
Highly Active Antibacterial Ferrocenoylated or Ruthenocenoylated Arg-‐Trp Peptides can be Discovered by an L-‐to-‐D Substitution Scan
by
H. Bauke Albada, Pascal Prochnow, Sandra Bobersky, Julia E. Bandow, Nils Metzler-‐Nolte*
Contents:
MALDI-‐TOF MS data of the FcC(O)-‐ and RcC(O)-‐WRWRW-‐NH2 peptides (Table S1) p. 2
HPLC-‐traces of the RcC(O)-‐WRWRW-‐NH2 peptides p. 3–13
Electronic Supplementary Material (ESI) for Chemical Science.This journal is © The Royal Society of Chemistry 2014
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Table S1. MALDI-‐TOF m/z-‐values for the FcC(O)-‐ and RcC(O)-‐WRWRW-‐NH2 peptides (FW = formula weight; EM = exact monoisotopic mass).
peptide FcC(O)-‐WRWRW-‐NH2 RcC(O)-‐WRWRW-‐NH2 [M+H]+ [M+H]+
found calculated (FW)
calculated (EM)
found calculated (FW)
calculated (EM)
LLLLL 1100.36a 1101.09 1100.47 1146.27a 1146.31 1146.44
LLLLD 1100.64 1101.09 1100.47 1146.38 1146.31 1146.44 LLLDL 1100.64 1101.09 1100.47 1146.38 1146.31 1146.44 LLDLL 1100.62 1101.09 1100.47 1146.38 1146.31 1146.44 LDLLL 1100.62 1101.09 1100.47 1146.38 1146.31 1146.44 DLLLL 1100.64 1101.09 1100.47 1146.38 1146.31 1146.44 LLLDD 1100.62 1101.09 1100.47 1146.39 1146.31 1146.44 LLDLD 1100.62 1101.09 1100.47 1146.38 1146.31 1146.44 LDLLD 1100.62 1101.09 1100.47 1146.38 1146.31 1146.44 DLLLD 1100.64 1101.09 1100.47 1146.38 1146.31 1146.44 LLDDL 1100.65 1101.09 1100.47 1146.39 1146.31 1146.44 LDLDL 1100.66 1101.09 1100.47 1146.38 1146.31 1146.44 DLLDL 1100.66 1101.09 1100.47 1146.38 1146.31 1146.44 LDDLL 1100.66 1101.09 1100.47 1146.37 1146.31 1146.44 DLDLL 1100.66 1101.09 1100.47 1146.39 1146.31 1146.44 DDLLL 1100.65 1101.09 1100.47 1146.38 1146.31 1146.44 LLDDD 1100.65 1101.09 1100.47 1146.38 1146.31 1146.44 LDLDD 1100.65 1101.09 1100.47 1146.38 1146.31 1146.44 DLLDD 1100.65 1101.09 1100.47 1146.37 1146.31 1146.44 LDDLD 1100.65 1101.09 1100.47 1146.37 1146.31 1146.44 DLDLD 1100.62 1101.09 1100.47 1146.37 1146.31 1146.44 DDLLD 1100.64 1101.09 1100.47 1146.37 1146.31 1146.44 LDDDL 1100.66 1101.09 1100.47 1146.37 1146.31 1146.44 DLDDL 1100.66 1101.09 1100.47 1146.37 1146.31 1146.44 DDLDL 1100.66 1101.09 1100.47 1146.37 1146.31 1146.44 DDDLL 1100.66 1101.09 1100.47 1146.37 1146.31 1146.44 LDDDD 1100.65 1101.09 1100.47 1146.38 1146.31 1146.44 DLDDD 1100.65 1101.09 1100.47 1146.37 1146.31 1146.44 DDLDD 1100.66 1101.09 1100.47 1146.37 1146.31 1146.44 DDDLD 1100.66 1101.09 1100.47 1146.39 1146.31 1146.44 DDDDL 1100.66 1101.09 1100.47 1146.37 1146.31 1146.44 DDDDD 1100.64 1101.09 1100.47 1146.11a 1146.31 1146.44
a these m/z-‐values were obtained by ESI-‐MS before, and are taken from: H. B. Albada, A.-‐I. Chiriac, M. Wenzel, M. Penkova, J. E. Bandow, H.-‐G. Sahl, N. Metzler-‐Nolte, Beilstein J. Org. Chem. 2012, 8, 1753.
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HPLC-‐traces of the L-‐to-‐D substituted RcC(O)-‐WRWRW-‐NH2 peptides
Conditions: Analytical HPLC was performed on an automated HPLC system using a C18-‐AQ RP column (250 × 4.6 mm) at a flow-‐rate of 1 mL/min. A linear gradient of 5% buffer B per min was started after 5 min of buffer A (A: H2O/MeCN/TFA, 95:5:0.1, v/v/v; B: MeCN/H2O/TFA, 95:5:0.1, v/v/v).
RcC(O)-‐LLLLL-‐NH2 (20.1 min)
RcC(O)-‐LLLLD-‐NH2 (19.8 min)
Minutes
0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40
mAU
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mAU
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1500UV [Channel 1] 0-fr1.dat
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0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40
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1500UV [Channel 1] 1-fr2.dat
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RcC(O)-‐LLLDL-‐NH2 (19.9 min)
RcC(O)-‐LLDLL-‐NH2 (19.8 min)
RcC(O)-‐LDLLL-‐NH2 (19.8 min)
Minutes
0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40
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UV [Channel 1] 2.dat
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UV [Channel 1] 3.dat
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UV [Channel 1] 4.dat
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RcC(O)-‐DLLLL-‐NH2 (19.9 min)
RcC(O)-‐LLLDD-‐NH2 (19.7 min)
RcC(O)-‐LLDLD-‐NH2 (19.4 min)
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UV [Channel 1] 5.dat
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UV [Channel 1] 12.dat
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UV [Channel 1] 13.dat
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RcC(O)-‐LDLLD-‐NH2 (19.9 min)
RcC(O)-‐DLLLD-‐NH2 (19.8 min)
RcC(O)-‐LLDDL-‐NH2 (19.8 min)
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UV [Channel 1] 14.dat
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UV [Channel 1] 15.dat
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UV [Channel 1] 23.dat
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RcC(O)-‐LDLDL-‐NH2 (19.6 min)
RcC(O)-‐DLLDL-‐NH2 (19.7 min)
RcC(O)-‐LDDLL-‐NH2 (19.7 min)
Minutes
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UV [Channel 1] 24.dat
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UV [Channel 1] 25.dat
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UV [Channel 1] 34.dat
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RcC(O)-‐DLDLL-‐NH2 (19.7 min)
RcC(O)-‐DDLLL-‐NH2 (19.7 min)
RcC(O)-‐LLDDD-‐NH2 (19.8 min)
Minutes
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UV [Channel 1] 35.dat
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UV [Channel 1] 45-2.dat
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UV [Channel 1] 123.dat
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RcC(O)-‐LDLDD-‐NH2 (19.8 min)
RcC(O)-‐DLLDD-‐NH2 (19.6 min)
RcC(O)-‐LDDLD-‐NH2 (19.5 min)
Minutes
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UV [Channel 1] 124.dat
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UV [Channel 1] 125.dat
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UV [Channel 1] 134.dat
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RcC(O)-‐DLDLD-‐NH2 (19.5 min)
RcC(O)-‐DDLLD-‐NH2 (19.8 min)
RcC(O)-‐LDDDL-‐NH2 (19.6 min)
Minutes
0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40
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UV [Channel 1] 135.dat
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UV [Channel 1] 145.dat
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UV [Channel 1] 234.dat
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RcC(O)-‐DLDDL-‐NH2 (19.9 min)
RcC(O)-‐DDLDL-‐NH2 (19.4 min)
RcC(O)-‐DDDLL-‐NH2 (19.6 min)
Minutes
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UV [Channel 1] 235.dat
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UV [Channel 1] 245.dat
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UV [Channel 1] 345.dat
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RcC(O)-‐LDDDD-‐NH2 (19.9 min)
RcC(O)-‐DLDDD-‐NH2 (19.8 min)
RcC(O)-‐DDLDD-‐NH2 (19.8 min)
Minutes
0 2 4 6 8 10 12 14 16 18 20 22 24 26 28 30 32 34 36 38 40
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UV [Channel 1] 1234.dat
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UV [Channel 1] 1235.dat
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UV [Channel 1] 1245.dat
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RcC(O)-‐DDDLD-‐NH2 (19.8 min)
RcC(O)-‐DDDDL-‐NH2 (19.9 min)
RcC(O)-‐DDDDD-‐NH2 (20.1 min)
Minutes
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UV [Channel 1] 1345.dat
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UV [Channel 1] 2345.dat
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UV [Channel 1] 12345-1.dat
