Chiral amplification by polypeptides and its relevance to prebiotic catalysis

Chemical Communications

Volumn , Issue 18, 2004, Pages 2021-2022

  Kelly, David H ^a   Meek, Alastair ^b   Roberts, Stanley M ^b  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF LIVERPOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

CHALCONE; LEUCINE; MONOMER; POLYLEUCINE; POLYPEPTIDE; PREBIOTIC AGENT; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; ENANTIOMER; ENANTIOSELECTIVITY; EPOXIDATION; POLYMERIZATION; PROTEIN SYNTHESIS; REACTION ANALYSIS; STRUCTURE ANALYSIS; TECHNIQUE;

EID: 6344278286     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b404379k     Document Type: Article

References (14)

1. B. L. Feringa and R. A. van Delden, Angew. Chem., Int. Ed., 1999, 38, 3418.
2. J. Jacques, A. Collet and S. H. Wilen, Enantiomers, Racemates and Resolutions, Wiley Interscience, New York, 1981, pp. 53-88.
3. P. A. Bentley, R. W. Flood, S. M. Roberts, J. Skidmore, C. B. Smith and J. A. Smith, Chem. Commun., 2001, 1616.
4. 1,3-Diaminopropane (8.1 μl, 0.2 mmol) was added dropwise to L-Leu-NCA (0.8 g, 5.1 mmol) and D-Leu-NCA (1.2 g, 7.6 mmol) in THF (30 ml) which was stirred under a nitrogen atmosphere for 4 days. The white solid was filtered off, extracted with the following solvents (50 ml) for 30 min each: water, acetone-water (1:1), acetone-water (4:1), acetone (×2), ethyl acetate (×2) and diethyl ether (×2), and dried under high vacuum overnight (1.25 g, 87%).
5. If a peptide chain has an N-terminal L-residue, will it preferentially react with a L-NCA monomer or a D-NCA monomer? Most studies indicate that there is a weak preference for homocoupling: T. Hitz and P. L. Luisi, Helv. Chim. Acta, 2002, 85, 3975; H. R. Kricheldorf and T. Mang, Makromol. Chem., 1981, 182, 3077.
6. If a peptide chain has an N-terminal L-residue, will it preferentially react with a L-NCA monomer or a D-NCA monomer? Most studies indicate that there is a weak preference for homocoupling: T. Hitz and P. L. Luisi, Helv. Chim. Acta, 2002, 85, 3975; H. R. Kricheldorf and T. Mang, Makromol. Chem., 1981, 182, 3077.
7. A similar analysis of two-step reactions was made by K. Soai, H. Hori and M. Kawahara, J. Chem. Soc., Chem Commun., 1992, 106, and (added after submission) for polymerisations:
8. T. H. Hitz and P. L. Luisi, Origins Life Evol. Biosphere, 2004, 34, 93.
9. This analysis is fundamentally the same as that proposed by Kagan: D. Guillaneux, S.-H. Zhao, O. Samuel, D. Rainford and H. B. Kagan, J. Am. Chem. Soc., 1994, 116, 9430, but we are proposing a new way to calculate the proportions of the homo- and hetero-chiral constituents (Kagan's α and β variables).
10. 31 - 1. The standard binary numbers were padded with zeros on the left and converted to 31 character strings, in which O represents the L-enantiomer and 1 the D-enantiomer. The individual examples were extracted (RightS) and analysed using standard string commands. A Microsoft® Visual Basic 3.0 program, in which chain length, catalytic site length and enantiomeric excess are definable variables is available from D. R. K. All other calculations were performed in Microsoft® Excel.
11. A. Berkessel. N. Gasch, K. Glaubitz and C. Koch, Org. Lett., 2001, 3, 3839.
12. Described in the previous paper in this issue.
13. H. Furano, T. Hanamoto, Y. Sugimoto and J. Inanaga, Org. Lett., 2000, 2, 49.
14. W. A. Bonner, Origins Life Evol. Biosphere, 1999, 29, 615.