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Chemical name: 2-(((9H-fluoren-9-yl)methoxy)carbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid // Synonyms: N-Fmoc-2-azabicyclo[2.1.1.]hexane-1-carboxylic acid, N-Fmoc-2-carboxy-2,4-methanopyrrolidine, N-Fmoc-2,4-methanoproline
|Molecular weight:||349,39 g/mol|
2,4-Methanoproline can be used for the replacement of D- or L-proline. It can easily be incorporated during solid phase peptide synthesis. The rigid bicyclic skeleton of 2,4-methanoproline strongly promotes the formation of a trans-amide conformation compared to D- or L-proline and thus behaves more like primary a-amino acids. This compound also serves as tool to investigate the effect of the amide bond conformation on activity. Please also see the Boc protected derivative BAA4580.
Escaping from Flatland: Substituted Bridged Pyrrolidine Fragments with Inherent Three-Dimensional Character; B. Cox, V. Zdorichenko, P. B. Cox, K. I. Booker-Milburn, R. Paumier, L. D. Elliott, M. Robertson-Ralph, and G. Bloomfield; ACS Med. Chem. Lett. 2020; 11: 1185-1190. https://doi.org/10.1021/acsmedchemlett.0c00039.
A Peptidyl-Prolyl Model Study: How Does the Electronic Effect Influence the Amide Bond Conformation? P. K. Mykhailiuk, V. Kubyshkin, T. Bach, N. Budisa; J. Org. Chem. 2017; 82: 8831-8841. https://doi.org/10.1021/acs.joc.7b00803.
Bradykinin and angiotensin II analogs containing a conformationally constrained proline analog; P. Juvvadi, D. J. Dooley, C. C. Humblet, G. H. Lu, E. A. Lunney, R. L. Panek, R. Skeean, G. A. Marshall; Int. J. Peptide Protein Res. 1992; 40: 163-170. https://doi.org/10.1111/j.1399-3011.1992.tb00289.x.
Conformational Properties of 2,4-Methanoproline (2-Carboxy-2,4-methanopyrrolidine) in Peptides: Evidence for 2,4-Methanopyrrolidine Asymmetry Based on Solid-State X-ray Crystallography, 1H NMR in Aqueous Solution, and CNDO/2 Conformational Energy Calculations; S. Talluri, G. T. Montelione, G. van Duyne, L. Piela, J. Clardy, H. A. Scheraga; J. Am. Chem. Soc. 1987; 109: 4473-4477. https://doi.org/10.1021/ja00249a008
Conformational Properties of 2,4-Methanoproline (2-Carboxy-2,4-methanopyrrolidine) in Peptides: Determination of Preferred Peptide Bond Conformation in Aqueous Solution by Proton Overhauser Measurements; G. T. Montelione, P. Hughes, J. Clardy, H. A. Scheraga; J. Am. Chem. Soc. 1986; 108: 6765-6773. https://doi.org/10.1021/ja00281a051.
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