Supporting Information
The crystal structures are deposited in Cambridge Structural Database under the following IDs: 5- CCDC1443104, 6- CCDC1443105, 8- CCDC1443103, 9- CCDC1443102. The crystal structure of 7 have already been discussed in [35] and the deposit number was CCDC1042476. The structure files can be retrieved free of charge at http://www.ccdc.cam.ac.uk.
| Supporting Information File 1: Experimental procedures, values for the amide rotational barriers in different solvents, copies of the NMR spectra and ellipsoid diagrams of the X-ray crystal structures. | ||
| Format: PDF | Size: 1.6 MB | Download |
Cite the Following Article
cis–trans-Amide isomerism of the 3,4-dehydroproline residue, the ‘unpuckered’ proline
Vladimir Kubyshkin and Nediljko Budisa
Beilstein J. Org. Chem. 2016, 12, 589–593.
https://doi.org/10.3762/bjoc.12.57
How to Cite
Kubyshkin, V.; Budisa, N. Beilstein J. Org. Chem. 2016, 12, 589–593. doi:10.3762/bjoc.12.57
Download Citation
Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window
below.
Citation data in RIS format can be imported by all major citation management software, including EndNote,
ProCite, RefWorks, and Zotero.
Presentation Graphic
| Picture with graphical abstract, title and authors for social media postings and presentations. | ||
| Format: PNG | Size: 252.3 KB | Download |
Citations to This Article
Up to 20 of the most recent references are displayed here.
Scholarly Works
- Schnitzer, T.; Trapp, N.; Fischer, L.-M.; Wennemers, H. Crystal structure analysis of N-acetylated proline and ring size analogs. Journal of peptide science : an official publication of the European Peptide Society 2023, 29, e3473. doi:10.1002/psc.3473
- Chernykh, A. V.; Aloshyn, D.; Kuchkovska, Y. O.; Daniliuc, C. G.; Tolmachova, N. A.; Kondratov, I. S.; Zozulya, S.; Grygorenko, O. O.; Haufe, G. Impact of β-perfluoroalkyl substitution of proline on the proteolytic stability of its peptide derivatives. Organic & biomolecular chemistry 2022, 20, 9337–9350. doi:10.1039/d2ob01430k
- Yang, Y.; Hansen, L. Optimized Fmoc-Removal Strategy to Suppress the Traceless and Conventional Diketopiperazine Formation in Solid-Phase Peptide Synthesis. ACS omega 2022, 7, 12015–12020. doi:10.1021/acsomega.2c00214
- Mykhailiuk, P. K. Fluorine-Containing Prolines: Synthetic Strategies, Applications, and Opportunities. The Journal of organic chemistry 2022, 87, 6961–7005. doi:10.1021/acs.joc.1c02956
- Kubyshkin, V. Polarity effects in 4-fluoro- and 4-(trifluoromethyl)prolines. Beilstein journal of organic chemistry 2020, 16, 1837–1852. doi:10.3762/bjoc.16.151
- Elbatrawi, Y. M.; Pedretty, K. P.; Giddings, N.; Woodcock, H. L.; Del Valle, J. R. δ-Azaproline and Its Oxidized Variants. The Journal of organic chemistry 2020, 85, 4207–4219. doi:10.1021/acs.joc.9b03384
- Mosesso, R.; Dougherty, D. A.; Lummis, S. C. R. Proline Residues in the Transmembrane/Extracellular Domain Interface Loops Have Different Behaviors in 5-HT3 and nACh Receptors. ACS chemical neuroscience 2019, 10, 3327–3333. doi:10.1021/acschemneuro.9b00315
- Nikitin, K.; O'Gara, R. Mechanisms and Beyond: Elucidation of Fluxional Dynamics by Exchange NMR Spectroscopy. Chemistry (Weinheim an der Bergstrasse, Germany) 2019, 25, 4551–4589. doi:10.1002/chem.201804123
- Xie, J.; Wu, Y.-Y.; Zhang, T.-Y.; Zhang, M.-Y.; Peng, F.; Lin, B.; Zhang, Y.-X. New antimicrobial compounds produced by endophytic Penicillium janthinellum isolated from Panax notoginseng as potential inhibitors of FtsZ. Fitoterapia 2018, 131, 35–43. doi:10.1016/j.fitote.2018.10.006
- Kubyshkin, V.; Pridma, S. O.; Budisa, N. Comparative effects of trifluoromethyl- and methyl-group substitutions in proline. New Journal of Chemistry 2018, 42, 13461–13470. doi:10.1039/c8nj02631a
- Priem, C.; Geyer, A. Synthetic Marine Sponge Collagen by Late-Stage Dihydroxylation. Organic letters 2017, 20, 162–165. doi:10.1021/acs.orglett.7b03525
- Mykhailiuk, P. K.; Kubyshkin, V.; Bach, T.; Budisa, N. Peptidyl-Prolyl Model Study: How Does the Electronic Effect Influence the Amide Bond Conformation?. The Journal of organic chemistry 2017, 82, 8831–8841. doi:10.1021/acs.joc.7b00803
- Kubyshkin, V.; Durkin, P.; Budisa, N. Energetic contribution to both acidity and conformational stability in peptide models. New Journal of Chemistry 2016, 40, 5209–5220. doi:10.1039/c5nj03611a
