siderophores: amphibactin-t and moanachelin ala-b 7klv of ... · bschool of chemistry, yachay tech,...
TRANSCRIPT
S1
An Efficient Solid-Phase Strategy for Total Synthesis of Naturally Occurring Amphiphilic Marine
Siderophores: Amphibactin-T and Moanachelin ala-B
Prabhakar Cherkupally,a Suhas Ramesh,a Thavendran Govender,a Hendrik G.
Kruger,a Beatriz G. de la Torre,a,b* Fernando Albericioa,b,c,d,e,f*
aCatalysis and Peptide Research Unit, School of Health Sciences, University of Kwazulu-Natal,
Durban 4001, South AfricabSchool of Chemistry, Yachay Tech, Yachay City of Knowledge, 100119-Urcuqui, EcuadorcSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4001, South AfricadInstitute for Research in Biomedicine-Barcelona (IRB-Barcelona), 08028-Barcelona, SpaineCIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine,
Barcelona Science Park, 08028 Barcelona, SpainfDepartment of Organic Chemistry, University of Barcelona, 08028-Barcelona, Spain
e-mails: [email protected]; [email protected]; [email protected] (FA)
and [email protected] (BGT)
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.This journal is © The Royal Society of Chemistry 2015
S2
S2 Table of contents
S3 Crude HPLC profile of Fmoc-L-Orn-OBn▪TFA (3)
S4 1H NMR & 13C NMR copies of Fmoc-L-Orn-OBn▪TFA (3)
S5 HRMS (ESI-QTOF) profile of Fmoc-L-Orn-OBn▪TFA (3)
S6 1H NMR & 13C NMR copies of Fmoc-L-Orn(Ac,OBz)-OBn (4)
S7 HRMS (ESI-QTOF) profile of Fmoc-L-Orn(Ac,OBz)-OBn (4)
S8 1H NMR & 13C NMR copies of Fmoc-L-Orn(Bz)-OBn (5)
S9 HRMS (ESI-QTOF) profile of Fmoc-L-Orn(Bz)-OBn (5)
S10 1H NMR & 13C NMR copies of Fmoc-L-Orn(Ac,OBz)-OH (1)
S11 HRMS (ESI-QTOF) profile of Fmoc-L-Orn(Ac,OBz)-OH (1)
S12 LCMS profiles of model peptide ‘DA-Lys-Ser-Orn(Ac,OH)-OH’
S13 Purified HPLC profile of amphibactin-T
S14 HRMS (ESI-QTOF) profile of amphibactin-T
S15 Purified HPLC profile of moanachelin ala-B
S16 HRMS (ESI-QTOF) profile of moanachelin ala-B
S3
Crude HPLC profile of Fmoc-L-Orn-OBn▪TFA (3)
HPLC ConditionsColumn: Phenomenex column C18 (3 µm x 4.6 x 50 mm)Eluent: 5 - 95% CH3CN / 0.1% TFA in 15 min Sol. A:100% H2O/0.1% TFA, Sol. B: 100% CH3CN/0.1% TFAWavelength: 220 nm Flow rate: 1 mL/ min
8.684
S4
1H NMR & 13C NMR copies of Fmoc-L-Orn-OBn▪TFA (3)
H2O
S5
HRMS (ESI-QTOF) profile of Fmoc-L-Orn-OBn▪TFA (3); Calc. for C27H28N2O4 445.2121,
found 445.2167.
S6
1H NMR & 13C NMR copies of Fmoc-L-Orn(Ac,OBz)-OBn (4)
H2O
S7
HRMS (ESI-QTOF) profile of Fmoc-L-Orn(Ac,OBz)-OBn (4); Calc. for C36H34N2O7 607.2438,
found 607.2403.
S8
1H NMR & 13C NMR copies of Fmoc-L-Orn(Bz)-OBn (5)
H2O
S9
HRMS (ESI-QTOF) profile of Fmoc-L-Orn(Bz)-OBn (5); Calc. for C34H32N2O5 549.2383, found
549.2342.
S10
1H NMR & 13C NMR copies of Fmoc-L-Orn(Ac,OBz)-OH (1)
H2O
S11
HRMS (ESI-QTOF) profile of Fmoc-L-Orn(Ac,OBz)-OH (1); Calc. for Calc. for C29H28N2O7
517.1969, found 517.1975.
S12
Model peptide: DA-Lys-Ser-Orn(Ac,OBz)-OH; Calc. for C33H53N5O9 663.3843, found 664;
DA-Lys-Ser-Orn(Ac,OH)-OH; Calc. for C26H49N5O8 559.3581, found 560 (M+1).
530 540 550 560 570 580 590 600 610 620 630 640 650 660 670 680 690 m/z0.0
0.1
0.2
0.3
0.4
0.5
0.6
0.7
0.8
0.9
1.0
1.1
1.2
1.3
1.4
1.5
Inten.(x10,000,000)
664
560
561
450 500 550 600 650 700 750 800 850 900 950 1000 1050 1100 m/z0.0
0.5
1.0
1.5
2.0
2.5
3.0
3.5
4.0
4.5
5.0
5.5
6.0
6.5
7.0
7.5
8.0
Inten.(x1,000,000)
560
DA-Lys-Ser-Orn(Ac,OH)-OH
DA-Lys-Ser-Orn(Ac,OH)-OH
DA-Lys-Ser-Orn(Ac,OBz)-OH
LCMS profile of crude model peptide after debenzoylation with 25% NH3 in MeOH
LCMS profile of crude model peptide after debenzoylation
with 1 M LiOH in THF/MeOH
S13
Purified HPLC profile of amphibactin-T
Prep-HPLC ConditionsColumn: Phenomenex C18 column (10 µm x 10 x 250 mm)Eluent: 5 - 60% CH3CN / 0.1% TFA in 30 min Sol. A: 100% H2O/0.1% TFA, Sol. B: 100% CH3CN/0.1% TFAWavelength: 220 nm Flow rate: 7 mL/ min
8.862
S14
HRMS (ESI-QTOF) profile of amphibactin-T; Calc. for C36H65N7O13 804.4713, found
804.4707.
S15
Purified HPLC profile of moanachelin ala-B
Prep-HPLC ConditionsColumn: Phenomenex C18 column (10 µm x 10 x 250 mm)Eluent: 5 - 60% CH3CN / 0.1% TFA in 30 min Sol. A: 100% H2O/0.1% TFA, Sol. B: 100% CH3CN/0.1% TFAWavelength: 220 nm Flow rate: 7 mL/ min
9.045
S16
HRMS (ESI-QTOF) profile of moanachelin ala-B; Calc. for C36H65N7O12 788.4763, found
788.4770.