A facile, efficient and racemization-free method for the synthesis of N-protected β-amino alcohols and peptaibols using N-hydroxysuccinimide active esters is described. Using this method, dipeptide, tripeptide and pentapeptide alcohols were isolated in high yields. The conformations in crystals of β-amino alcohol, dipeptide and tripeptide alcohols were analysed, with a well-defined type III β-turn being observed in the tripeptide alcohol crystals. This method is found to be compatible with Fmoc-, Boc- and other side-chain protecting groups.
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http://dx.doi.org/10.1039/c0ob01226b | DOI Listing |
Spectrochim Acta A Mol Biomol Spectrosc
January 2025
School of Chemistry and Chemical Engineering, Linyi University, Linyi 276005, PR China. Electronic address:
Normal levels of HOCl can resist pathogen invasion and maintain cellular redox balance. However, excessive HOCl can easily harm the ecological environment and human health. Establishing a reliable approach for detection of HOCl can help resolve controversial issues regarding HOCl in physiological systems and help detect HOCl in complex environmental water samples.
View Article and Find Full Text PDFOrg Lett
January 2025
Department of Chemistry, University of Science and Technology of China, 96 Jinzhai Road, Hefei, Anhui 230026, China.
The visible-light-mediated continuous dehydration condensation and oxidative radical dimerization, featuring sulfur hexafluoride (SF) as both a condensation agent and oxidant, have been developed. This photocatalytic method uses commercially available N-protected amino acids as substrates and enables the formation of azlactone monomers and dimers, facilitating efficient utilization and degradation of greenhouse gas SF.
View Article and Find Full Text PDFChemMedChem
December 2024
School of Chemistry, University College Dublin, Dublin, D04 N2E2, Ireland.
Inspired by the cyclopentenone family of prostaglandins, a series of 4-aza, cross-conjugated cyclopentenones is described. Synthesised from N-protected (4R)-aza-cyclopentenone 5, the exocyclic alkene was installed using a modified Baylis-Hillman type aldol reaction, whereby carbon-carbon bond formation is accompanied by dehydration. In this manner octanal and octenal, for example, can be introduced to mimic the ω-group present in the natural prostaglandins.
View Article and Find Full Text PDFChemistry
November 2024
Department of Chemistry, Dalhousie University, 6274 Coburg Road, P.O. Box 15000, Halifax, Nova Scotia, B3H 4R2, Canada.
The aryloxyamine motif is a prominent pharmacophore in drug design and development. While these biologically relevant structures could in principle be sustainably assembled from the base metal-catalyzed O-arylation of inexpensive and abundant amino alcohols with (hetero)aryl chlorides, reports of such challenging C-O bond formations with useful scope are lacking. In response, we report herein the hitherto unknown Ni-catalyzed C-O cross-coupling of N-protected amino alcohols (primary, secondary, and tertiary) with (hetero)aryl chlorides.
View Article and Find Full Text PDFCommun Chem
November 2024
Department of Chemistry, Gwangju Institute of Science and Technology, Gwangju, Republic of Korea.
Alteration of a well-established reaction mechanism for access to different molecular structures is an inherently intriguing research subject. In that context, syn-stereospecific alkene dihalogenation draws attention as a long-standing problem in synthetic organic chemistry. The simplest approach would be the incorporation of an additional stereo-inverting step within the traditional anti-dihalogenation process.
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