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Fmoc-2,4-methanoproline

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

Product code:FAA8470
CAS No.:1936396-62-1
Formula:C21H19NO4
Molecular weight:349,39 g/mol
Grouped product items
Qty Packing unit Price SKU
1 g
$810.00
FAA8470.0001
5 g
$3,240.00
FAA8470.0005
Safety Data Sheets
description

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.


references

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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