Synthesis of enantiopure 7-substituted azepane-2-carboxylic acids as templates for conformationally constrained peptidomimetics
European Journal of Organic Chemistry, ISSN: 1434-193X, Vol: 2012, Issue: 11, Page: 2133-2141
2012
- 37Citations
- 21Captures
Metric Options: Counts1 Year3 YearSelecting the 1-year or 3-year option will change the metrics count to percentiles, illustrating how an article or review compares to other articles or reviews within the selected time period in the same journal. Selecting the 1-year option compares the metrics against other articles/reviews that were also published in the same calendar year. Selecting the 3-year option compares the metrics against other articles/reviews that were also published in the same calendar year plus the two years prior.
Example: if you select the 1-year option for an article published in 2019 and a metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019. If you select the 3-year option for the same article published in 2019 and the metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019, 2018 and 2017.
Citation Benchmarking is provided by Scopus and SciVal and is different from the metrics context provided by PlumX Metrics.
Example: if you select the 1-year option for an article published in 2019 and a metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019. If you select the 3-year option for the same article published in 2019 and the metric category shows 90%, that means that the article or review is performing better than 90% of the other articles/reviews published in that journal in 2019, 2018 and 2017.
Citation Benchmarking is provided by Scopus and SciVal and is different from the metrics context provided by PlumX Metrics.
Article Description
The introduction of a cyclic amino acid in a peptide is one of the best methods to rigidify a strand. A general approach towards a new class of seven-membered ring amino acids is described starting from (S)-tribenzyl glutamic acid γ-aldehyde, which reacts with β-keto phosphonates to generate the Horner-Wadsworth-Emmons product. In the presence of H and a Pd catalyst, a four-step process occurs involving double-bond hydrogenation, hydrogenolysis of three benzyl protecting groups, imine formation, and reductive amination to produce the 7-substituted azepane carboxylic acid in good overall yield and with good to excellent diastereomeric ratios. An amino function can be introduced in the 7-position as an additional orthogonal chemical handle for readily generating diversity on the cyclic amino acid scaffold by using a β-keto phosphonate derived from amino acids. A cyclic RGD (Arg-Gly-Asp) pentapeptide analogue containing this new class of noncoded amino acids was also prepared by microwave-assisted cyclization, showing a promising activity as α β integrin inhibitor. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Bibliographic Details
Provide Feedback
Have ideas for a new metric? Would you like to see something else here?Let us know