Design and Solid Phase Synthesis of New DOTA Conjugated (+)-Biotin Dimers Planned to Develop Molecular Weight-Tuned Avidin Oligomers
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1 Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2015 Supplementary Information Design and Solid Phase Synthesis of New DTA Conjugated (+)-Biotin Dimers Planned to Develop Molecular Weight-Tuned Avidin ligomers Alessandro Pratesi, Mauro Ginanneschi, Fabrizio Melani, Marco Chinol, Angela Carollo, Giovanni Paganelli, Marco Lumini, Mattia Bartoli, Marco Frediani, Luca Rosi, Giorgio Petrucci, Luigi Messori, and Anna Maria Papini Contents: Potential energy data for molecular modelling studies Sinthesis and characterization of Fmoc-Lys-tBu Bis-biotins characterization via HPLC-ESI-MS MALLS correlation functions S1
2 Figure 1S. Structures of bis-biotins designed for the molecular modeling study. In brackets is reported the linker arm length (Å) between the two amide C= of the biotin residues, calculated on the fully extended planar conformation. S2
3 Table 1S. Potential energy data for type 1 complex. 150 K 300 K 450 K Entry Ep Ep Ep sd sd (Kcal/mol) (Kcal/mol) (Kcal/mol) sd bis-biotins with non-peg spacers bis-biotins with PEG spacers Type 1 Complex: potential energy average from 50 conformations recorded at a constant temperature (Ep) and standard deviation (sd) recorded during dynamic simulations. The structures 1 and 2 are the same in both series. S3
4 Table 2S. Potential energy data for type 2 complex. 150 K 300 K 450 K Entry Ep Ep Ep sd sd (Kcal/mol) (Kcal/mol) (Kcal/mol) sd bis-biotins with non-peg spacers bis-biotins with PEG spacers Type 2 complex: potential energy average from 50 conformations recorded at a constant temperature (Ep) and standard deviation (sd) recorded during dynamic simulations. The structures 1 and 2 are the same in both series S4
5 Scheme 1S. Synthetic route for compound 3. H N CH (Boc) 2 DMAP tbuh H N CtBu AcEt TFA H N CtBu 1 HN HN 2 NH 2 3 Synthesis of tert-butyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-aminohexanoate (Fmoc-Lys-tBu, 3). 2.0 g of Fmoc-L-Lys(Boc)-H (1) were added with 2.33 g of di-terbuthyl dicarbonate, Boc 2, and mg of 4-dimethylaminopiridine, DMAP, in 30 ml of anhydrous tert-buthanol. The reaction was stirred for 30 min at 35 C and for 15h at room temperature. At the end of the reaction the product, 2, was checked by TLC (AcEt/exane 2:1), R f = The solvent was removed under vacuum and the solid residue was dissolved 30 ml of ethyl acetate and 5 ml of water; the organic layer was washed with a saturated solution of NaHC 3 (20 ml for 3 times), and with water (20 ml for 3 times). The organic phase was dried with anhydrous Na 2 S 4, the solvent was removed under vacuum and the crude product was purified by direct-phase LC on silica gel using AcEt/exane 30: g of the purified product 2 were dissolved in 56 ml of a solution containing 28 of TFA in AcEt. The solution was stirred at 45 C for 1h. After, another 10 ml of TFA were added. The reaction was stirred for 2h and at the end TFA was removed under nitrogen flow. The crude compound 3, was solubilized in 10 ml of CH 3 CN/H 2 2:3 and purified by solid phase extraction on reverse-phase C18 silica gel, obtaining the pure compound Fmoc-Lys-tBu (3) (311 mg, 57 yield). 1 H NMR (298 K), δ (DMS, 200 MHz): (m, 2H), (m, 2H) (m, 4H), (m, 2H), 1.65 (m, 2H), (m, 15H). ESI-MS: calculated m/z [M+H] + ; found S5
6 Figure 2S. 1 H-NMR spectrum of compound 3 (200 MHz, DMS). S6
7 AP_BB-1_2_ : Diode Array Range: e-1 AU 5.0e-1 2.5e AP_BB-1_2_ TIC 7.93e Time AP_BB-1_2_ (3.082) Cm (289:304) e m/z Figure 3S. HPLC-MS analysis of 6. Method: 15 to 50 of eluent B in 5 min; flow 0.6 ml/min. Rt= 3.12 min HPLC purity >98.8 ESI-MS analysis - m/z: [M+H] ; [M+2H] ; [M+3H] S7
8 AP_BisBio-6a : Diode Array Range: 9.816e-1 AU 5.0e AP_BisBio-6a TIC 6.00e Time AP_BisBio-6a 324 (3.364) Cm (320:332) e m/z Figure 4S. HPLC-MS analysis of 9. Method: 15 to 50 of eluent B in 5 min; flow 0.6 ml/min. Rt= 3.46 min HPLC purity >98.5 ESI-MS analysis - m/z: [M+H] ; [M+2H] ; [M+3H] S8
9 AP_BisBio : Diode Array Range: AU 0.0 AP_BisBio TIC 1.49e Time AP_BisBio (3.448) Cm (327:348) e m/z Figure 5S. HPLC-MS analysis of 11. method: 20 to 60 of eluent B in 5 min; flow 0.6 ml/min. Rt = 3.54 min HPLC purity >99 ESI-MS analysis - m/z: [M+H] ; [M+2H] ; [M+3H] S9
10 AP_BisBio : Diode Array Range: AU AP_BisBio TIC e Time AP_BisBio (3.505) Cm (332:361) e m/z Figure 6S. HPLC-MS analysis of 14. method: 20 to 60 of eluent B in 5 min; flow 0.6 ml/min. Rt = 3.61 min HPLC purity >99 ESI-MS analysis - m/z: [M+2H] ; [M+3H] S10
11 AP_BB7_ : Diode Array Range: AU 5.0e AP_BB7_ TIC 1.62e Time AP_BB7_ (3.435) Cm (324:340) e m/z Figure 7S. HPLC-MS analysis of 16. method: 20 to 50 of eluent B in 5 min; flow 0.6 ml/min. Rt = 3.36 min HPLC purity 99 ESI-MS analysis - m/z: [M+H] ; [M+2H] S11
12 AP_BB8_ : Diode Array Range: AU 5.0e AP_BB8_ TIC 1.46e8-15 Time AP_BB8_ (3.498) Cm (330:347) e m/z Figure 8S. HPLC-MS analysis of 18. method: 20 to 50 of eluent B in 5 min; flow 0.6 ml/min. Rt = 3.42 min HPLC purity 98 ESI-MS analysis - m/z: [M+H] ; [M+2H] S12
13 Figure 9S. Correlation function of native avidin, experimental data are showed as black dots, while the result of interpolation is showed as red line. S13
14 Figure 10S. Correlation function for Av/16 complexes, experimental data are showed as black dots, while the result of interpolation is showed as red line. A) t R min; B) t R 9.44 min; C) t R 8.54 min; D) t R 8.11 min. S14
15 Figure 11S. Correlation functions of Av/18 polymer at different incubation time: A) 0 min.; B) 45 min; C) 150 min.; D) 360 min. S15
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