Conformational flexibility and absolute stereochemistry of (3R)-3-hydroxy-4-aryl-β-lactams investigated by chiroptical properties and TD-DFT calculations

Chirality

Volumn 24, Issue 9, 2012, Pages 741-750

  Tedesco, Daniele ^a   Zanasi, Riccardo ^b   Guerrini, Andrea ^c   Bertucci, Carlo ^a  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

^c National Research Centre   (Italy)

Author keywords

lactam sector rules; lactams; absolute configuration; conformational flexibility; electronic circular dichroism; molecular geometry; optical rotation; time dependent density functional theory

Indexed keywords

3 HYDROXY 4 ARYL BETA LACTAM DERIVATIVE; AMIDE; BETA LACTAM DERIVATIVE; UNCLASSIFIED DRUG;

ATOM; CHROMATOPHORE; CIRCULAR DICHROISM; CONFERENCE PAPER; DRUG STRUCTURE; PRIORITY JOURNAL; STEREOCHEMISTRY;

BETA-LACTAMS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OPTICAL PROCESSES; QUANTUM THEORY; STEREOISOMERISM;

EID: 84865636956     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.22043     Document Type: Conference Paper

References (62)

1. Lukacs G, Ohno M, editors. Recent progress in the chemical synthesis of antibiotics. Berlin: Springer-Verlag; 1990.
2. Morin RB, Gorman M, editors. Chemistry and biology of β-lactam antibiotics, vol. 1-3. New York: Academic Press; 1982.
3. Sammes PG, editor. Topics in antibiotic chemistry, vol. 3. New York: Ellis Horwood; 1980.
4. O'Sullivan J, Abraham EP,. Biosynthesis of β-lactam antibiotics. In:, Corcoran JW, editor. Antibiotics, vol. 4, biosynthesis. Berlin: Springer-Verlag; 1982. p. 101-122.
5. Bentley PM, Southgate R, editors. Recent advances in the chemistry of β-lactam antibiotics. London: The Royal Society of Chemistry; 1989.
6. Christensen BG,. Structure-activity relationships in β-lactam antibiotics. In:, Salton MRJ, Shockman GD, editors. β-Lactam antibiotics. New York: Academic Press; 1981. p. 101-122.
7. Burnett DA, Caplen MA, Davis HR, Burrier RE, Clader JW,. 2-azetidinones as inhibitors of cholesterol absorption. J Med Chem 1994; 37: 1733-1736. (Pubitemid 24219762)
8. Braun M, Galle D,. A simple stereoselective synthesis of the cholesterol absorption inhibitor (-)-SCH 48461. Synthesis 1996; 1996: 819-820. (Pubitemid 26248130)
9. Chen LY, Zaks A, Chackalamannil S, Dugar S,. Asymmetric synthesis of substituted 2-azaspiro[3.5]nonan-1-ones: an enantioselective synthesis of the cholesterol absorption inhibitor (+)-SCH 54016. J Org Chem 1996; 61: 8341-8343. (Pubitemid 26400936)
10. Adlington RM, Baldwin JE, Becker GW, Chen B, Cheng L, Cooper SL, Hermann RB, Howe TJ, McCoull W, McNulty AM, Neubauer BL, Pritchard GJ,. Design, synthesis, and proposed active site binding analysis of monocyclic 2-azetidinone inhibitors of prostate specific antigen. J Med Chem 2001; 44: 1491-1508. (Pubitemid 32852193)
11. Ojima I,. β-Lactam synthon method: Enantiomerically pure β-lactams as synthetic intermediates. In:, Georg GI, editor. The organic chemistry of β-lactam antibiotics. New York: VCH; 1992a. p. 197-255.
12. Ojima I, Habus I, Zhao M, Zucco M, Park YH, Sun CM, Brigaud T,. New and efficient approaches to the semisynthesis of taxol and its C-13 side chain analogs by means of β-lactam synthon method. Tetrahedron 1992b; 48: 6985-7012.
13. Ojima I,. Recent advances in the β-lactam synthon method. Acc Chem Res 1995; 28: 383-389.
14. Ojima I, Delaloge F,. Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the β-lactam synthon method. Chem Soc Rev 1997; 26: 377-386. (Pubitemid 127680899)
15. Palomo C, Aizpurua JM, Ganboa I, Oiarbide M,. β-Lactams as versatile intermediates in α- and β-amino acid synthesis. Synlett 2001; 2001: 1813-1826. (Pubitemid 33135256)
16. Barbaro G, Battaglia A, Guerrini A, Bertucci C,. One-pot synthesis of (3R)-hydroxy-β-lactams via enolates of 2-tert-butyl-1,3-dioxolan-4-ones. Part 1. Tetrahedron: Asymmetry 1997; 8: 2527-2531. (Pubitemid 27356944)
17. Barbaro G, Battaglia A, Guerrini A, Bertucci C,. (3R)-Chiral control of 3-alkyl-3-hydroxy-β-lactams via addition reaction of imines to enolates of 1,3-dioxolan-4-ones. J Org Chem 1999a; 64: 4643-4651.
18. Barbaro G, Battaglia A, Di Giuseppe F, Giorgianni P, Guerrini A, Bertucci C, Geremia S,. New efficient synthesis of (3R,4S)-3-methyl-3-hydroxy-4-phenyl- β-lactam. Tetrahed Asym 1999b; 10: 2765-2773.
19. Battaglia A, Guerrini A, Bertucci C,. Synthesis of optically active constrained 2-substituted norstatines: a straightforward application of Seebach's "SRS" synthetic principle. J Org Chem 2004; 69: 9055-9062. (Pubitemid 40004025)
20. Seebach D, Sting AR, Hoffmann M,. Self-regeneration of stereocenters (SRS)-applications, limitations, and abandonment of a synthetic principle. Angew Chem Int Ed Engl 1996; 35: 2708-2748. (Pubitemid 27080126)
21. Rehling H, Jensen H,. Circulardichroismus und absolute Konfiguration von β-Lactamen. Tetrahed Lett 1972; 13: 2793-2796.
22. Ong EC, Cusachs LC, Weigang Jr OE,. Sector rules for rotatory strength of low symmetry chromophores: lactones, lactams, and peptides. J Chem Phys 1977; 67: 3289-3297.
23. Polonski T, Milewska MJ,. Optical activity of lactones and lactams. 5. Long-wavelength circular dichroism of β-thiolactams (2-azetidinethiones). Croat Chim Acta 1989; 62: 129-134.
24. Galle D, Tolksdorf M, Braun M,. Circular dichroism of trans and cis β-lactams and of their inclusion compounds in β-cyclodextrin. Tetrahed Lett 1995; 36: 4217-4220.
25. Djerassi C,. Optical rotatory dispersion: applications to organic chemistry. New York: McGraw-Hill; 1960.
26. Moffitt W, Woodward RB, Moscowitz A, Klyne W, Djerassi C,. Structure and the optical rotatory dispersion of saturated ketones. J Am Chem Soc 1961; 83: 4013-4018.
27. Lightner DA,. The octant rule. In:, Berova N, Nakanishi K, Woody R, editors. Circular dichroism: principles and applications, 2nd ed. New York: Wiley-VCH; 2000. p. 261-303.
28. Boyd D, Riehl J, Richardson F,. Chiroptical properties of 1-carbapenam and orbital mixing in nonplanar amides. Tetrahedron 1979; 35: 1499-1508.
29. McCann J, Rauk A, Shustov GV, Wieser H, Yang D,. Electronic and vibrational circular dichroism of model β-lactams: 3-methyl- and 4-methylazetidin-2-one. Appl Spectrosc 1996; 50: 630-641. (Pubitemid 126595712)
30. Śysek R, Borsuk K, Chmielewski M, Kałuża Z, Urbańczyk-Lipkowska Z, Klimek A, Frelek J,. 5-Dethia-5-oxacephams: toward correlation of absolute configuration and chiroptical properties. J Org Chem 2002; 67: 1472-1479. (Pubitemid 34211589)
31. Frelek J, Kowalska P, Masnyk M, Kazimierski A, Korda A, Woźnica M, Chmielewski M, Furche F,. Circular dichroism and conformational dynamics of cephams and their carba and oxa analogues. Chem Eur J 2007; 13: 6732-6744. (Pubitemid 47230987)
32. Huang X, Rickman BH, Borhan B, Berova N, Nakanishi K,. Zinc porphyrin tweezer in host-guest complexation: determination of absolute configurations of diamines, amino acids, and amino alcohols by circular dichroism. J Am Chem Soc 1998; 120: 6185-6186. (Pubitemid 28307015)
33. Berova N, Nakanishi K,. Exciton chirality method: principles and applications. In:, Berova N, Nakanishi K, Woody R, editors. Circular dichroism: principles and applications, 2nd ed. New York: Wiley-VCH; 2000. p. 337-382.
34. Petrovic AG, Chen Y, Pescitelli G, Berova N, Proni G,. CD-sensitive Zn-porphyrin tweezer host-guest complexes, part 1: MC/OPLS-2005 computational approach for predicting preferred interporphyrin helicity. Chirality 2010; 22: 129-139.
35. Chen Y, Petrovic AG, Roje M, Pescitelli G, Kayser MM, Yang Y, Berova N, Proni G,. CD-sensitive Zn-porphyrin tweezer host-guest complexes, part 2: Cis- and trans-3-hydroxy-4-aryl/alkyl-β-lactams. A case study. Chirality 2010; 22: 140-152.
36. Barbaro G, Battaglia A, Guerrini A, Bertucci C,. Assessment of the absolute configuration of a series of (3R)-3-hydroxy-3-alkyl-β-lactams. Tetrahedron: Asymmetry 1998; 9: 3401-3409. (Pubitemid 28529551)
37. Bauernschmitt R, Ahlrichs R,. Treatment of electronic excitations within the adiabatic approximation of time dependent density functional theory. Chem Phys Lett 1996; 256: 454-464. (Pubitemid 126160745)
38. Hohenberg P, Kohn W,. Inhomogenous electron gas. Phys Rev 1964; 136: B864-B871.
39. Kohn W, Sham LJ,. Self-consistent equations including exchange and correlation effects. Phys Rev 1965; 140: A1133-A1138.
40. Spartan'02. Irvine, CA, USA: Wavefunction, Inc; 2002.
41. Halgren TA,. MMFF VI. MMFF94s option for energy minimization studies. J Comput Chem 1999; 20: 720-729. (Pubitemid 129652635)
42. Becke AD,. Density-functional thermochemistry. V. Systematic optimization of exchange-correlation functionals. J Chem Phys 1997; 107: 8554-8560. (Pubitemid 127611634)
43. Grimme S,. Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J Comput Chem 2006; 27: 1787-1799. (Pubitemid 44672561)
44. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ,. Gaussian 09, Revision A.02. Wallingford, CT: Gaussian, Inc.; 2009.
45. Dunning TH,. Gaussian basis functions for use in molecular calculations. III. Contraction of (10s6p) atomic basis sets for the first-row atoms. J Chem Phys 1971; 55: 716-723.
46. Huzinaga S,. Gaussian-type functions for polyatomic systems. I. J Chem Phys 1965; 42: 1293-1302.
47. McLean AD, Chandler GS,. Contracted Gaussian basis sets for molecular calculations. I. Second row atoms, Z = 11-18. J Chem Phys 1980; 72: 5639-5648.
48. Huzinaga S,. Approximate atomic functions. II. Edmonton: Department of Chemistry, University of Alberta; 1971.
49. Tomasi J, Mennucci B, Cammi R,. Quantum mechanical continuum solvation models. Chem Rev 2005; 105: 2999-3094.
50. Humphrey W, Dalke A, Schulten K,. VMD: visual molecular dynamics. J Mol Graphics 1996; 14: 33-38. (Pubitemid 26152973)
51. Ditchfield R, Hehre WJ, Pople JA,. Self-consistent molecular orbital methods. IX. An extended Gaussian-type asis for molecular orbital studies of organic molecules. J Chem Phys 1971; 54: 724-728.
52. Hehre WJ, Ditchfield R, Pople JA,. Self-consistent molecular orbital methods. XII. Further extensions of Gaussian-type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys 1972; 56: 2257-2261.
53. Hariharan PC, Pople JA,. The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chem Acc 1973; 28: 213-222.
54. Gordon MS,. The isomers of silacyclopropane. Chem Phys Lett 1980; 76: 163-168.
55. Frisch MJ, Pople JA, Binkley JS,. Self-consistent molecular orbital methods. XXV. Supplementary functions for Gaussian basis sets. J Chem Phys 1984; 80: 3265-3269.
56. Autschbach J,. Computing chiroptical properties with first-principles theoretical methods: background and illustrative examples. Chirality 2009; 21: E116-E152.
57. Perdew JP, Burke K, Ernzerhof M,. Generalized gradient approximation made simple. Phys Rev Lett 1996; 77: 3865-3868. (Pubitemid 126631804)
58. Perdew JP, Burke K, Ernzerhof M,. Generalized gradient approximation made simple [Phys. Rev. Lett. 77, 3865 (1996)]. Phys Rev Lett 1997; 78: 1396-1396.
59. Adamo C, Barone V,. Toward reliable density functional methods without adjustable parameters: the PBE0 model. J Chem Phys 1999; 110: 6158-6170.
60. Stephens PJ, Harada N,. ECD Cotton effect approximated by the Gaussian curve and other methods. Chirality 2010; 22: 229-233.
61. Taylor JR,. Introduction to error analysis: the study of uncertainties in physical measurements, 2nd ed. Sausalito: University Science Books; 1997.
62. Pescitelli G, Di Bari L, Berova N,. Conformational aspects in the studies of organic compounds by electronic circular dichroism. Chem Soc Rev 2011; 40: 4603-4625.