Detection of the chirality of Cα-methylated α-amino acids with a dynamic helical poly(phenylacetylene) bearing aza-18-crown-6 ether pendants

Chirality

Volumn 18, Issue 9, 2006, Pages 717-722

  Morino, Kazuhide ^a   Kaptein, Bernard ^b   Yashima, Eiji ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b DSM RESEARCH   (Netherlands)

Author keywords

Amino acids; Chirality; Circular dichroism; Helix; Optically active; Polyacetylenes

Indexed keywords

AMINO ACID DERIVATIVE; CARBON; CROWN ETHER DERIVATIVE; METHYL GROUP; NORVALINE; PHENYLACETYLENE; POLYPHENYLACETYLENE DERIVATIVE; UNCLASSIFIED DRUG; VALINE;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CIRCULAR DICHROISM; COMPLEX FORMATION; ENANTIOMER; METHYLATION; PRIORITY JOURNAL; ULTRAVIOLET SPECTROSCOPY;

ACETYLENE; AMINO ACIDS; CIRCULAR DICHROISM; CROWN ETHERS; ETHERS, CYCLIC; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 33748768722     PISSN: 08990042     EISSN: 1520636X     Source Type: Journal    
DOI: 10.1002/chir.20303     Document Type: Article

References (65)

1. (a) Bonner WA. Origins of chiral homogeneity in nature. Top Stereochem 1988;18:1-96.
2. (b) Keszthelyi LQ. Origin of the homochirality of biomolecules. Rev Biophys 1995;28:473-507.
3. (c) Avalos M, Babiano R, Cintas P, Jimenez JL, Palacios JC. From parity to Chirality: chemical implications revisited. Tetrahedron: Asymmetry 2000;11:2845-2874.
4. (a) Rikken GLJA, Raupach E. Enantioselective magnetochiral photochemistry. Nature 2000;405:932-935.
5. (b) Rau H. Asymmetric photochemistry in solution Chem Rev 1983;83:535-547.
6. (c) Inoue Y. Asymmetric photochemical reactions in solution Chem Rev 1992;92:741-770.
7. (d) Avalos M, Babiano R, Cintas P, Jiménez JL, Palacios JC, Barron LD. Absolute asymmetric synthesis under physical fields: facts and fictions Chem Rev 1998;98:2391-2404.
8. (e) Berger R, Gottselig M, Quack M, Willeke M. Parity violation dominates the dynamics of chirality in dichlorodisulfane Angew Chem Int Ed 2001;40:4195-4198.
9. (a) Bailey J, Chrysostomou A, Hough JH, Gledhill TM, McCall A, Clark S, Ménard F, Tamura M. Circular polarization in star-formation regions: implications for biomolecular homochirality. Science 1998;281:672-674.
10. (b) Nishino H, Kosaka A, Hembury GA, Shitomi H, Onuki H, Inoue Y. Mechanism of pH-dependent photolysis of aliphatic amino acids and enantiomeric enrichment of racemic leucine by circular polarized light. Org Lett 2001;3:921-924.
11. Kvenvolden K, Lawless J, Pering K, Peterson E, Flores J, Ponnamperuma C, Kaplan IR, Moore C. Evidence for extraterrestrial amino-acids and hydrocarbons in the Murchison meteorite. Nature 1970;228:923-926.
12. Cronin JR, Pizzarello S, Epstein S, Krishnamurthy RV. Molecular and isotopic analyses of the hydroxy acids, dicarboxylic acids, and hydroxydicarboxylic acids of the Murchison meteorite. Geochim Cosmochim Acta 1993;57:4745-4752.
13. Cooper WC, Onwo WM, Cronin JR. Alkyl phosphonic acids and sulfonic acids in the Murchison meteorite. Geochim Cosmochim Acta 1992;56:4109-4115.
14. (a) Cronin JR, Pizzarello S. Amino acids of the Murchison meteorite. III. Seven carbon acyclic primary α-amino acids. Geochim Cosmochim Acta 1986;50:2419-2427.
15. (b) Cronin JR, Pizzarello S. Enantiomeric excesses in meteoritic amino acids. Science 1997;275:951-955.
16. (c) Pizzarello S, Cronin JR. Non-racemic amino acids in the Murray and Murchison meteorites. Geochim Cosmochim Acta 2000;64:329-338.
17. (d) Pizzarello S, Zolensky M, Turk KA. Nonracemic isovaline in the Murchison meteorites: chiral distribution and mineral association. Geochim Cosmochim Acta 2003;67:1589-1595.
18. Meierhenrich UJ, Caro GMM, Bredehöft JH, Jessberger EK, Thiemann WHP. Identification of diamino acids in the Murchison meteorites. Proc Natl Acad Sci USA 2004;101:9182-9186.
19. (a) Podlech J. New insight into the source of biomolecular homochirality: an extraterrestrial origin for molecules of life. Angew Chem Int Ed 1999;38:477-478.
20. (b) Strasdeit H. New studies on the Murchison shed light on the pre-RNA world. Chem Bio Chem 2005;6:801-803.
21. (a) Bada JL, Miller SL. Racemization and the origin of optically active organic compounds in living organisms. Biosystems 1987;20:21-26.
22. (b) Cohen BA, Chyba CF. Racemization of meteoritic amino acids Icarus 2000;145:272-281.
23. Pizzarello S, Weber AL. Prebiotic amino acids as asymmetric catalyst. Science 2004;303:1151.
24. α-methylated α-amino acids and the homochirality of life: searching for a link. Angew Chem Int Ed 2004;43:6695-6699.
25. (a) Yashima E, Matsushima T, Okamoto Y. Chirality assignment of amines and amino alcohols based on circular dichroism induced by helix formation of a stereoregular poly((4-carboxyphenyl)acetylene) through acid-base complexation. J Am Chem Soc 1997;119:6345-6359.
26. (b) Yashima E, Maeda K, Okamoto Y. Memory of macromolecular helicity assisted by interaction with achiral small molecules. Nature 1999;399:449-451.
27. (c) Saito MA, Maeda K, Onouchi H, Yashima E. Synthesis and macromolecular helicity induction of a stereoregular polyacetylene bearing a carboxy group with natural amino acids in water. Macromolecules 2000;33:4616-4618.
28. (d) Maeda K, Morino K, Okamoto Y, Sato T, Yashima E. Mechanism of Helix induction on a stereoregular poly((4-carboxyphenyl)acetylene) with chiral amines and memory of the macromolecular helicity assisted by interaction with achiral amines. J Am Chem Soc 2004;126:4329-4342.
29. (e) Morino K, Watase N, Maeda K, Yashima E. Chiral amplification in macromolecular helicity assisted by noncovalent interaction with achiral amines and memory of the helical chirality. Chem Eur J 2004;10:4703-4707.
30. (f) Hasegawa T, Morino K, Tanaka Y, Katagiri H, Furusho Y, Yashima E. Temperature-driven switching of helical chirality of poly((4-carboxyphenyl) acetylene) induced by a single amidine enantiomer and memory of the diastereomeric macromolecular helicity. Macromolecules 2006;39:482-488.
31. (a) Yashima E, Nimura T, Matsushima T, Okamoto Y. Poly((4- dihydroxyborophenyl)acetylene) as a novel probe for chirality and structural assignments of various kinds of molecules including carbohydrates and steroids by circular dichroism. J Am Chem Soc 1996;118:9800-9801.
32. (b) Kawamura H, Maeda K, Okamoto Y, Yashima E. Molecular recognition of nucleosides and nucleotides based on circular dichroism induced by helix formation of poly((4-dihydroxyborophenyl)acetylene) Chem Lett 2001;30:58-59.
33. (a) Onouchi H, Maeda K, Yashima E. A helical polyelectrolyte induced by specific interactions with biomolecules in Water. J Am Chem Soc 2001;123:7441-7442.
34. (b) Onouchi H, Kashiwagi D, Hayashi K, Maeda K, Yashima E. Helicity induction on poly(phenylacetylene)s bearing phosphonic acid pendants with chiral amines and memory of the macromolecular helicity assisted by interaction with achiral amines in dimethyl sulfoxide. Macromolecules 2004;37:5495-5503.
35. (c) Onouchi H, Miyagawa T, Furuko A, Maeda K, Yashima E. Enantioselective esterification of prochiral phosphonate pendants of a polyphenylacetylene assisted by macromolecular helicity: storage of a dynamic macromolecular helicity memory. J Am Chem Soc 2005;127:2960-2965.
36. (d) Miyagawa T, Furuko A, Maeda K, Katagiri H, Furusho Y, Yashima E. Dual memory of enantiomeric helices in a polyacetylene induced by a single enantiomer. J Am Chem Soc 2005;127:5018-5019.
37. Onouchi H, Hasegawa T, Kashiwagi D, Ishiguro H, Maeda K, Yashima E. Helicity induction in charged poly(phenylacetylene)s bearing various acidic functional groups in water and its mechanism. Macromolecules 2005;38:8625-8633.
38. (a) Yashima E, Maeda Y, Matsushima T, Okamoto Y. Preparation of polyacetylenes bearing an amino group and their application to chirality assignment of carboxylic acids by circular dichroism. Chirality 1997;9:593-600.
39. (b) Maeda K, Takeyama Y, Sakajiri K, Yashima E. Nonracemic dopant-mediated hierarchical amplification of macromolecular helicity in a charged polyacetylene leading to a cholesteric liquid crystal in water. J Am Chem Soc 2004;126:16284-16285.
40. (c) Nagai K, Maeda K, Takeyama Y, Sakajiri K, Yashima E. Helicity induction and chiral amplification in a poly(phenylacetylene) bearing N,N-diisopropylaminomethyl groups with chiral acids in water. Macromolecules 2005;38:5444-5451.
41. (a) Yashima E. Chiral and chirality discrimination on helical polyacetylenes. Anal Sci 2002;18:3-6.
42. (b) Yashima E, Maeda K, Nishimura T. Detection and amplification of chirality by helical polymers. Chem Eur J 2004;10:42-51.
43. (a) Nonokawa R, Yashima E. Detection and amplification of a small enantiomeric imbalance in α-amino acids by a helical poly(phenylacetylene) with crown ether pendants. J Am Chem Soc 2003;125:1278-1283.
44. (b) Nonokawa R, Yashima E. Helicity induction on a poly(phenylacetylene) derivative bearing aza-18-crown-6 ether pendants in water. J Polym Sci Polym Chem 2003;41:1004-1013.
45. (c) Nonokawa R, Oobo M, Yashima E. Helicity induction on a poly(phenylacetylene) derivative bearing aza-15-crown-5 ether pendants in organic solvents and water. Macromolecules 2003;36:6599-6606.
46. (d) Morino K, Oobo M, Yashima E. Helicity induction in a poly(phenylacetylene) bearing aza-18-crown-6 ether pendants with optically active bis(amino acid)s and its chiral stimuli-responsive gelation. Macromolecules 2005;38:3461-3468. For other examples of crown ether-bound helical polymers, see 19.
47. (e) Sakai R, Satoh T, Kakuchi R, Kaga H, Kakuchi T. Macromolecular helicity induction for novel optically inactive poly (phenyl isocyanate) bearing crown ether based on the host-guest complexation. Macromolecules 2003;36:3709-3713. 19.
48. (f) Sakai R, Satoh T, Kakuchi R, Kaga H, Kakuchi T. Helicity induction of polyisocyanate with a crown cavity on the main chain synthesized by cyclopolymerization of α,ω-diisocyanate. Macromolecules 2004;37:3996-4003.
49. Crisma M, Barazza A, Formaggio F, Kaptein B, Broxterman QB, Kamphuis J, Toniolo C. Peptaibolin: synthesis, 3D-structure, and membrane modifying properties and the natural antibiotic and selected analogues. Tetrahedron 2001;57:2813-2825.
50. (a) 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.
51. (b) Zahn S, Canary JW. Absolute configuration of N,N-dialkyl α-amino acids and β-amino alcohols from exciton-coupled circular dichroism spectra of Cu(II) complexes. Org Lett 1999;1:861-864.
52. (c) Tsukube H, Shinoda S, Uenishi J, Kanatani T, Itoh H, Shiode M, Iwachido T, Yonemitsu O. Molecular recognition with lanthanide(III) tris(β-diketonate) complexes: extraction, transport, and chiral recognition of unprotected amino acids. Inorg Chem 1998;37:1585-1591.
53. (d) Leipert D, Nopper D, Bauser M, Gauglitz G, Jung G. Investigation of the molecular recognition of amino acids by cyclopeptides with reflectometric interference spectroscopy. Angew Chem Int Ed 1998;37:3308-3311.
54. (e) Mizutani T, Sakai N, Yagi S, Takagishi T, Kitagawa S, Ogoshi H. Allosteric chirality amplification in zinc bilinone dimer. J Am Chem Soc 2000;122:748-749.
55. (f) Mizuno Y, Aida T, Yamaguchi K. Chirality-memory molecule: crystallographic and spectroscopic studies on dynamic molecular recognition events by fully substituted chiral porphyrins. J Am Chem Soc 2000;122:5278-5285.
56. (g) Tsukube H, Fukui H, Shinnoda S. Synergistic binding and chirality sensing of unprotected amino acids with ferrocenecarboxylic acid-crown ether conjugate. Tetrahedron Lett 2001;42:7583-7585.
57. (h) Shinkai S, Ikeda M, Sugasaki A, Takeuchi M. Positive allosteric systems designed on dynamic supramolecular scaffolds: toward switching and amplification of guest affinity and selectivity. Ace Chem Res 2001;34:494-503.
58. (i) Canary JW, Holmes AE, Liu J. Prospects for circular dichroism detection of nonracemic extraterrestrial organic molecules. Enantiomer 2001;6:181-188.
59. (j) Huang X, Fujioka N, Koehn FE, Williamson RT, Nakanishi K, Berova N. Absolute configurational assignments of secondary amines by CD-sensitive dimeric zinc porphyrin. J Am Chem Soc 2002;124:10320-10335.
60. (a) Kabuto K, Sasaki Y. A facile NMR method assigning absolute configuration of underivatized α-methyl-α-amino acids using a chiral lanthanoid shift reagent for aqueous solution. Tetrahedron Lett 1990;31:1031-1034.
61. (b) Hulst R, de Vries NK, Feringa BL. Asymmetric synthesis of new chiral europium N,N′-disuccinate complexes: shift reagents for aqueous solutions and application in the enantiomeric excess determination of amino acids. J Org Chem 1994;59:7453-7458.
62. (a) Kruizinga WH, Bolster J, Kellogg RM, Kamphuis J, Boesten WHJ, Meijer EM, Schoemaker HE. Synthesis of optically pure α-alkylated α-amino acids and a single-step method for enantiomeric excess determination. J Org Chem 1988;53:1826-1827.
63. (b) Kaptein B, Boesten WHJ, Broxterman QB, Peters PJH, Schoemaker HE, Kamphuis J. Enzymatic resolution of α, α-disubstituted α-amino acid esters and amides. Tetrahedron: Asymmetry 1993;4:1113-1116.
64. (c) Sonke T, Kaptein B, Boesten WHJ, Broxterman QB, Kamphuis J, Formaggio F, Toniolo C, Rutjes FPJT, Schoemaker HE. Amino amidase catalyzed preparation and further transformations of enantiopure α-hydrogen- and α,α-disubstituted α-amino acids. In: Patel NK, editor. Stereoselective Biocatalysis. New York: Marcel Dekker; 2000. p 23-58.
65. Connors KA. Binding constants. New York: John Wiley; 1987.