Electronic Supplementary Information (ESI) for New Journal of Chemistry
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1 Electronic Supplementary Material (ESI) for New Journal of Chemistry. This journal is The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 018 Electronic Supplementary Information (ESI) for New Journal of Chemistry Bio-Activated Intramolecular Anti-Aza-Michael Addition: Stereoselective Synthesis of Hydantoin Derivatives Vedamurthy M. Bhusainahalli, a,b Antonio Rescifina,* c Nunzio Cardullo, a Carmela Spatafora a, and Corrado Tringali* a a Dipartimento di Scienze Chimiche, Università di Catania, Viale A. Doria - I-9515 Catania, Italy. b Vidyaherbs R&D Center for Excellence, 14B, Jigani Industrial Area, Phase-1 Anekal Taluk Bangalore India. c Dipartimento di Scienze del Farmaco, Università di Catania, Viale A. Doria - I-9515 Catania, Italy. Deceased. Table of Contents Spectroscopic characterization of 10 Spectroscopic characterization of 11 Spectroscopic characterization of 1 Spectroscopic characterization of 13 Spectroscopic characterization of 1 Spectroscopic characterization of 1 General procedure for reaction screening S S3 S8 S10 S13 S15 S1 Cartesian coordinates, energies, and frequencies for compounds and transition states, in water-saturated ethyl acetate, at M0-X level of theory S1 S1
2 Spectroscopic characterization of 10 Figure S1. ESI MS spectrum of 10. Figure S. 1 H NMR spectrum (500 MHz, CD 3OD) of 10. S
3 f1 (ppm) Figure S3. 13 C NMR spectrum (15 MHz, CD 3OD) of 10. Spectroscopic characterization of 11 Figure S4. ESI MS spectrum of 11. S3
4 Figure S5. 1 H NMR spectrum (500 MHz, CD 3OD) of 11. Figure S. 13 C NMR spectrum (15 MHz, CD 3OD) of 11. S4
5 f1 (ppm) f (ppm) Figure S. gdqf-cosy spectrum of 11. S5
6 Figure S8. ghsqcad spectrum of f1 (ppm) f (ppm) Figure S9. ghmbcad spectrum of 11. S
7 Figure S10. 1D NOESY of 11 irradiated at 4.05 ppm. Figure S11. 1D NOESY of 11 irradiated at 3.85 ppm. S
8 Figure S1. 1D NOESY of 11 irradiated at.35 ppm. Spectroscopic characterization of 1 Figure S13. ESI MS spectrum of 1. S8
9 Figure S14. 1 H NMR spectrum (500 MHz, CD 3COCD 3) of 1. Figure S C NMR spectrum (15 MHz, CD 3COCD 3) of 1. Spectroscopic characterization of 13 S9
10 Figure S1. 1 H NMR spectrum (500 MHz, CD 3OD) of f1 (ppm) Figure S1. 13 C NMR spectrum (15 MHz, CD 3OD) of 13. S10
11 Figure S18. gcosy spectrum of 13. S11
12 Figure S19. ghscqad spectrum of 13. Figure S0. ghmbcad spectrum of 13. S1
13 Spectroscopic characterization of 1 Figure S1. ESI MS spectrum of 1. Figure S. 1 H NMR spectrum (500 MHz, CD 3OD) of 1. S13
14 Figure S3. 13 C NMR spectrum (15 MHz, CD 3OD) of 1. S14
15 Spectroscopic characterization of 1 Figure S4. 1 H NMR spectrum (500 MHz, CD 3OD) of 1. Figure S5. 13 C NMR spectrum (15 MHz, CD 3OD) of 14. S15
16 General procedure for reaction screening Some parameters such as solvent, enzyme concentration and ph have been screened in order to find the best reaction conditions to obtain the hydantoin 11 starting from 10. The experiments performed have been summarized in Table S1. The urea 10 ( mg; 0.05 mmol) was solubilized in the organic solvent (1mL), then adding the TvL solution ( U/mL or 15 U/mL), previously prepared using acetate (0.1 M; ph 4.) or phosphate (0.1 M; ph.0) buffer. Each mixture was stirred at room temperature in uncapped vials for -4 h. For each experiment, a blank was carried out in the same conditions, without enzyme. The reactions ( µl, diluted to a final volume of 00 µl) were monitored at regular time intervals by HPLC (Agilent Series 100) equipped with a diode array detector (DAD; G1315D). An analytical reversed phase column (Luna C 18, 5 μm; mm; Phenomenex) was used to run reaction mixtures, eluting at 1 ml/min with the following gradient of CH 3CN/HCOOH (99:1 v/v; A) in H O/HCOOH (99:1 v/v; B): t 0 min A = 30%, t 10 min A = %, t 15 min A = %, t 0 min A = 30%. Table S1 Optimization of the reaction conditions for the synthesis of Hydantoin 11 a Entry Solvent TvL (U/mL) Time (h) Conversion (%) b Yield (%) b 1 EtOAc/buffer ph 4. EtOAc/buffer ph EtOAc/buffer ph.0 4 CHCl/buffer ph 4. 5 CHCl/buffer ph CHCl/buffer ph.0 buffer ph 4. 8 buffer ph buffer ph.0 10 Acetone/buffer ph Acetone/buffer ph EtOH/buffer ph EtOH/buffer ph a Conditions: caffeoyl urea 10 (mg/ml); the reactions were carried out at room temperature in uncapped vials. b The yield was determined by HPLC-UV S1
17 Cartesian coordinates, energies, and frequencies for compounds and transition states, in watersaturated ethyl acetate, at M0-X level of theory R Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z imaginary frequencies Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= RH1 Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S1
18 imaginary frequencies Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= RH1-TS Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z imaginary frequency: Zero-point correction= (Hartree/Particle) Thermal correction to Energy= 0.0 Thermal correction to Enthalpy= 0.10 Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= PH1 Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S18
19 imaginary frequencies Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= 0.90 Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= Z-P-exo Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S19
20 imaginary frequencies Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= E-P-exo Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z imaginary frequencies Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= RH Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S0
21 imaginary frequencies Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= 0.03 Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= RH-TS Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z imaginary frequency: Zero-point correction= 0.49 (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= S1
22 Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= PH Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z imaginary frequencies Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= 0.44 Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= P-endo Center Atomic Atomic Coordinates (Angstroms) Number Number Type X Y Z S
23 imaginary frequencies Zero-point correction= (Hartree/Particle) Thermal correction to Energy= Thermal correction to Enthalpy= Thermal correction to Gibbs Free Energy= Sum of electronic and zero-point Energies= Sum of electronic and thermal Energies= Sum of electronic and thermal Enthalpies= Sum of electronic and thermal Free Energies= S3
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