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Polypeptide Preparation by β-Lactone-Mediated Chemical Ligation.
Org Lett
July 2024
Department of Chemistry, University at Albany, State University of New York, 1400 Washington Avenue, Albany, NY 12222, USA.
Native chemical ligation (NCL) represents a cornerstone strategy in accessing synthetic peptides and proteins, remaining one of the most efficacious methodologies in this domain. The fundamental requisites for achieving a proficient NCL reaction involve chemoselective coupling between a C-terminal thioester peptide and a thiol-bearing N-terminal peptide. However, achieving coupling at sterically congested residues remains challenging.
View Article and Find Full Text PDFChromatographic separation by RPLC-ESI-MS of all hydroxyproline isomers for the characterization of collagens from different sources.
J Chromatogr A
April 2024
Department of Drug Sciences, University of Pavia, Viale Taramelli 12, Pavia 27100, Italy. Electronic address:
During collagen biosynthesis, proline is post-translationally converted to hydroxyproline by specific enzymes. This amino acid, unique to collagen, plays a crucial role in stabilizing the collagen triple helix structure and could serve as an important biomarker for collagen content and quality analysis. Hydroxyproline has four isomers, depending on whether proline is hydroxylated at position 4 or 3 and on whether the cis- or trans- conformation is formed.
View Article and Find Full Text PDFSimultaneous determination of total ergot alkaloids in wheat flour by Orbitrap mass spectrometry.
Food Chem
May 2024
Food Analysis Research Center, Korea Food Research Institute, Republic of Korea. Electronic address:
The optimization screening methods for total ergot alkaloids in wheat extracts involve transforming them into a single compound, which is then analyzed via high-resolution Orbitrap mass spectrometry (Orbitrap MS). Orbitrap MS provides highly sensitive and accurate mass measurements, enhancing the selectivity and sensitivity of the analysis. Various hydrolysis and reduction methods have been investigated, and the use of superhydrides has emerged as the most effective method for transforming ergopeptine alkaloids.
View Article and Find Full Text PDFNitroalkanes as thioacyl equivalents to access thioamides and thiopeptides.
Nat Commun
August 2023
School of Chemistry, and Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University, 710049, Xi'an, China.
Thioamides are an important, but a largely underexplored class of amide bioisostere in peptides. Replacement of oxoamide units with thioamides in peptide therapeutics is a valuable tactic to improve biological activity and resistance to enzymatic hydrolysis. This tactic, however, has been hampered by insufficient methods to introduce thioamide bonds into peptide or protein backbones in a site-specific and stereo-retentive fashion.
View Article and Find Full Text PDFThe Metabolism of Lufotrelvir, a Prodrug Investigated for the Treatment of SARS-COV2 in Humans Following Intravenous Administration.
Drug Metab Dispos
October 2023
Pfizer Worldwide Research, Development and Medical, Groton, Connecticut (R.S.O., K.S.); Pfizer Worldwide Research, Development and Medical, La Jolla, California (R.M.J.); Pfizer Worldwide Research, Development and Medical, Collegeville, Pennsylvania (N.C.); Pfizer Worldwide Research, Development and Medical, Pearl River, New York (S.S.T.); and The Netherlands Organization for Applied Scientific Research (T.N.O.), Zeist, Netherlands (E.v.D., P.A.S., I.M.B.)
The metabolism of lufotrelvir, a novel phosphate prodrug of PF-00835231 for the treatment of COVID-19, was evaluated in healthy human volunteers and clinical trial participants with COVID-19 following intravenous infusion. The prodrug was completely converted to PF-00835231 that was subsequently cleared by hydrolysis, hydroxylation, ketoreduction, epimerization, renal clearance, and secretion into the feces. The main circulating metabolite was a hydrolysis product (M7) that was present at concentrations greater than PF-00835231, and this was consistent between healthy volunteers and participants with COVID-19.
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