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N-primary-amine-terminal beta-turn tetrapeptides as organocatalysts for highly enantioselective aldol reaction.
J Org Chem. 2009 Jul 03; 74(13):4812-8.JO

Abstract

Tetrapeptides, containing a terminated primary amine and conformationally restricted D-Pro-Gly or D-Pro-Aib (2-aminoisobutanoic acid) segment as a strongly beta-turn-nucleating element, were designed and synthesized with condensation of N-module dipeptides with C-module dipeptides in solution. They were first applied to catalyze aldol reactions, and were found to be effective catalysts for the transformations. The tetrapeptide Val-D-Pro-Gly-Leu-OH (1g) was the optimal organocatalyst. It was shown that the intensive beta-turn conformation, indicated by CD and NOESY spectra, contributed to the (R)-aldol and high enantioselectivity of the reaction of acetone in MeOH, whereas the sharply varied conformation should contribute to the low enantioselectivity and (S)-product of the reaction in 1,2-dichloroethane (DCE). The asymmetric induction in the reaction of hydroxyacetone was not affected by solvents, and predominant anti products were achieved by 1g in MeCN with the additive (S)-BINOL.

Authors+Show Affiliations

Institute of Biochemistry & Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

19459650

Citation

Wu, Feng-Chun, et al. "N-primary-amine-terminal Beta-turn Tetrapeptides as Organocatalysts for Highly Enantioselective Aldol Reaction." The Journal of Organic Chemistry, vol. 74, no. 13, 2009, pp. 4812-8.
Wu FC, Da CS, Du ZX, et al. N-primary-amine-terminal beta-turn tetrapeptides as organocatalysts for highly enantioselective aldol reaction. J Org Chem. 2009;74(13):4812-8.
Wu, F. C., Da, C. S., Du, Z. X., Guo, Q. P., Li, W. P., Yi, L., Jia, Y. N., & Ma, X. (2009). N-primary-amine-terminal beta-turn tetrapeptides as organocatalysts for highly enantioselective aldol reaction. The Journal of Organic Chemistry, 74(13), 4812-8. https://doi.org/10.1021/jo9005766
Wu FC, et al. N-primary-amine-terminal Beta-turn Tetrapeptides as Organocatalysts for Highly Enantioselective Aldol Reaction. J Org Chem. 2009 Jul 3;74(13):4812-8. PubMed PMID: 19459650.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - N-primary-amine-terminal beta-turn tetrapeptides as organocatalysts for highly enantioselective aldol reaction. AU - Wu,Feng-Chun, AU - Da,Chao-Shan, AU - Du,Zhi-Xue, AU - Guo,Qi-Peng, AU - Li,Wei-Ping, AU - Yi,Lei, AU - Jia,Ya-Ning, AU - Ma,Xiao, PY - 2009/5/23/entrez PY - 2009/5/23/pubmed PY - 2009/11/7/medline SP - 4812 EP - 8 JF - The Journal of organic chemistry JO - J Org Chem VL - 74 IS - 13 N2 - Tetrapeptides, containing a terminated primary amine and conformationally restricted D-Pro-Gly or D-Pro-Aib (2-aminoisobutanoic acid) segment as a strongly beta-turn-nucleating element, were designed and synthesized with condensation of N-module dipeptides with C-module dipeptides in solution. They were first applied to catalyze aldol reactions, and were found to be effective catalysts for the transformations. The tetrapeptide Val-D-Pro-Gly-Leu-OH (1g) was the optimal organocatalyst. It was shown that the intensive beta-turn conformation, indicated by CD and NOESY spectra, contributed to the (R)-aldol and high enantioselectivity of the reaction of acetone in MeOH, whereas the sharply varied conformation should contribute to the low enantioselectivity and (S)-product of the reaction in 1,2-dichloroethane (DCE). The asymmetric induction in the reaction of hydroxyacetone was not affected by solvents, and predominant anti products were achieved by 1g in MeCN with the additive (S)-BINOL. SN - 1520-6904 UR - https://www.unboundmedicine.com/medline/citation/19459650/N_primary_amine_terminal_beta_turn_tetrapeptides_as_organocatalysts_for_highly_enantioselective_aldol_reaction_ DB - PRIME DP - Unbound Medicine ER -