Quantum mechanical origin of the conformational preferences of 4-thiaproline and its S-oxides

Amino Acids

Volumn 41, Issue 1, 2011, Pages 181-186

  Choudhary, Amit ^a   Pua, Khian Hong ^a   Raines, Ronald T ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

Collagen; N *interaction; Stereoelectronic effect; Thiazolidine

Indexed keywords

CARBONYL DERIVATIVE; OXYGEN; TIMONACIC;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL BOND; CHEMICAL INTERACTION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PEPTIDE ANALYSIS; PEPTIDE BOND; PRIORITY JOURNAL; PROTEIN CONFORMATION; QUANTUM MECHANICS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OXIDES; PROLINE; QUANTUM THEORY;

EID: 79960387273     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-010-0504-8     Document Type: Article

References (36)

1. Aitken RA, Mesher STE, Ross FC, Ryan BM (1997) Effect of added benzoic acid on the phase-transfer catalysed permanganate oxidation of organosulfur compounds. Synthesis 7:787-791 (Pubitemid 27342151)
2. Benzi C, Improta R, Scalmani G, Barone V (2002) Quantum mechanical study of the conformational behavior of proline and 4R-hydroxyproline dipeptide analogues in vacuum and in aqueous solution. J Comput Chem 23:341-350 (Pubitemid 34137474)
3. Choudhary A, Raines RT (2009) A donor-acceptor perspective on carbonyl-carbonyl interactions in proteins. In: Lebl M (ed) Breaking away: the proceedings of the twenty-first American peptide symposium. Prompt Scientific Publishing, San Diego, CA, pp 347-349
4. Choudhary A, Gandla D, Krow GR, Raines RT (2009) Nature of amide carbonyl-carbonyl interactions in proteins. J Am Chem Soc 131:7244-7246
5. DeRider ML, Wilkens SJ, Waddell MJ, Bretscher LE, Weinhold F, Raines RT, Markley JL (2002) Collagen stability: insights from NMR spectroscopic and hybrid density functional computational investigations of the effect of electronegative substituents on prolyl ring conformations. J Am Chem Soc 124:2497-2505 (Pubitemid 34251763)
6. Eberhardt ES, Panasik N Jr, Raines RT (1996) Inductive effects on the energetics of prolyl peptide bond isomerization: implications for collagen folding and stability. J Am Chem Soc 118:12261-12266 (Pubitemid 27006792)
7. Fischer E (1906) Untersuchungen über Aminosaüren, Polypeptide und Proteine. Ber Deutsch Chem Ges 39:530-610
8. Fischer FR, Wood PA, Allen FH, Diederich F (2008) Orthogonal dipolar interactions between amide carbonyl groups. Proc Natl Acad Sci USA 105:17290-17294
9. Glendening ED, Badenhoop JK, Reed AE, Carpenter JE, Bohmann JA, Morales CM, Weinhold F (2001) NBO 5.0. Theoretical Chemistry Institute. University of Wisconsin-Madison, Madison, WI
10. Goodman M, Niu GC-C, Su K-c (1970a) Conformational aspects of polypeptide structure. XXXII. Helical poly[(S)-thiazolidine-4-carboxylic acid]. Theoretical results. J Am Chem Soc 92:5219-5220
11. Goodman M, Su K-c, Niu GC-C (1970b) Conformational aspects of polypeptide structure. XXXII. Helical poly[(S)-thiazolidine-4-carboxylic acid]. Experimental results. J Am Chem Soc 92:5220-5222
12. Gorres KL, Raines RT (2010) Prolyl 4-hydroxylase. Crit Rev Biochem Mol Biol 45:106-124
13. Gorres KL, Edupuganti R, Krow GR, Raines RT (2008) Conforma-tional preferences of substrates for human prolyl 4-hydroxylase. Biochemistry 47:9447-9855
14. 1H Nuclear magnetic resonance studies of N-acetyl-L-proline N-methylamide. Molecular conformations, hydrogen bondings, and thermodynamic quantities in various solvents. Biopolymers 16:1259-1270 (Pubitemid 8111333)
15. Hinderaker MP, Raines RT (2003) An electronic effect on protein structure. Protein Sci 12:1188-1194 (Pubitemid 36597505)
16. Holmgren SK, Taylor KM, Bretscher LE, Raines RT (1998) Code for collagen's stability deciphered. Nature 392:666-667
17. Improta R, Benzi C, Barone V (2001) Understanding the role of stereoelectronic effects in determining collagen stability. 1. A quantum mechanical study of proline, hydroxyproline, and fluoroproline dipeptide analogues in aqueous solution. J Am Chem Soc 123:12568-12577 (Pubitemid 33143784)
18. Kern D, Schutkowski M, Drakenberg T (1997) Rotational barriers of cis/trans isomerization of proline analogues and their catalysis by cyclophilin. J Am Chem Soc 119:8403-8408 (Pubitemid 27404565)
19. Lesarri A, Cocinero EJ, López JC, Alonso JL (2005) Shape of 4S- and 4R-hydroxyproline in gas phase. J Am Chem Soc 127:2572-2579
20. Liang G-B, Rito CJ, Gellman SH (1992) Variations in the turn-forming characteristics of N-acyl proline units. Biopolymers 32:293-301
21. Matsuzaki T, Iitaka Y (1971) The crystal structure of acetyl-L-proline-N-methylamide. Acta Crystallogr B27:507-516
22. 3 receptor. J Phys Chem B 113:12148-12153
23. Milner-White JE, Bell LH, Maccallum PH (1992) Pyrrolidine ring puckering in cis and trans-proline residues in proteins and polypeptides. J Mol Biol 228:725-734
24. Nachtergaele WA, Anteunis MJO (1980) Ring conformational aspects of cis- and trans-N-acetyl-4-carbomethoxy-1, 3-thiazolidine-1-oxide. Bull Soc Chim Belg 89:749-758
25. Panasik N Jr, Eberhardt ES, Edison AS, Powell DR, Raines RT (1994) Inductive effects on the structure of proline residues. Int J Pept Protein Res 44:262-269 (Pubitemid 24292928)
26. Paulini R, Müller K, Diederich F (2005) Orthogonal multipolar interactions in structural chemistry and biology. Angew Chem Int Ed 44:1788-1805
27. Prabhakar YS, Solomon VR, Gupta MK, Katti SB (2006) QSAR studies on thiazolidines: a biologically priviliged scaffold. Top Heterocycl Chem 4:161-249
28. Shoulders MD (2009) Ph.D. thesis, University of Wisconsin-Madison
29. Shoulders MD, Kamer KJ, Raines RT (2009) Origin of the stability conferred upon collagen by fluorination. Bioorg Med Chem Lett 19:3859-3962
30. Tshuchishashi G-i, Mitamura S, Inoue S, Ogura K (1973) Asymmetric synthesis using a, b-unsaturated sulfoxides. A highly selective Michael reaction. Tetrahedron Lett 323-326
31. Ulshöfer R, Podlech J (2009) Stereoelectronic effects in vinyl sulfoxides. J Am Chem Soc 131:16618-16619
32. Weinhold F (1998) Natural bond orbital methods. In: PvR Schleyer, Allinger NL, Clark T, Gasteiger J, Kollman PA, Shaefer HF III et al (eds) Encyclopedia of computational chemistry, vol 3. John Wiley & Sons, Chichester, UK, pp 1792-1811
33. Weinhold F, Landis CR (2005) Valency and bonding: a natural bond orbital donor-acceptor perspective. Cambridge University Press, Cambridge, UK
34. Wendt M, Weinhold F (2001) NBOView 1.1. Theoretical Chemistry Institute. University of Wisconsin-Madison, Madison WI
35. Wittelsberger A, Keller M, Scarpellino L, Patiny L, Orbea-Acha H, Mutter M (2000) Pseudoprolines:targeting a cis conformation in a mimetic of the gp120 V3 loop of HIV-1. Angew Chem Int Ed 39:1111-1115 (Pubitemid 30217259)
36. Zhu W, Gincherman Y, Docherty P, Spilling CD, Becker DF (2002) Effects of proline analog binding on the spectroscopic and redox properties of PutA. Arch Biochem Biophys 408:131-136 (Pubitemid 36062544)