Welcome to Iris Biotech
For better service please confirm your country and language we detected.
Currency
EUR
Contact rapide
Veuillez m'envoyer plus d'informations sur
Fmoc-2,4-methanoproline
Nom chimique: 2-(((9H-fluoren-9-yl)methoxy)carbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid // Synonymes: N-Fmoc-2-azabicyclo[2.1.1.]hexane-1-carboxylic acid, N-Fmoc-2-carboxy-2,4-methanopyrrolidine, N-Fmoc-2,4-methanoproline
- n° Art.:FAA8470
- n° CAS:1936396-62-1
- Formule:C21H19NO4
- Storage temperature:2-8°C
- Masse moléculaire:349,39 g/mol
from 160,00 €
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.
Besoin d'informations supplémentaires sur ce produit?
entrer en contact
Brochures et dépliants
Des produits qui pourraient également vous intéresser!
