Welcome to Iris Biotech
For better service please confirm your country and language we detected.
Currency
USD
Quick contact
Please send me more information about
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
- Storage temperature:2-8°C
- Molecular weight:349.39 g/mol
from $200.00
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.
* Disclaimer
We refer to our general terms and conditions.
All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.
All information contained in our webshop is compiled to the best of our knowledge.
Prices and product availability are subject to change and require reconfirmation. Please contact us for further information.
Do you need further information about this product?
get in contact
Brochures & Flyers
We found other products you might like!
