Dipeptide analogues of fluorinated aminophosphonic acid sodium salts as moderate competitive inhibitors of cathepsin C

• Karolina Wątroba,
• Małgorzata Pawełczak and
• Marcin Kaźmierczak

Beilstein J. Org. Chem. 2023, 19, 434–439, doi:10.3762/bjoc.19.33

• Poznań, Uniwersytetu Poznańskiego 10, 61-614 Poznań, Poland 10.3762/bjoc.19.33 Abstract In this paper, we present the solvolysis reaction of dipeptide analogues of fluorinated aminophosphonates with simultaneous quantitative deprotection of the amino group. To the best of our knowledge, this work is the

• to the corresponding phosphonic acids or their salts is often a necessary step to measure activity in enzyme inhibition bioassays [16][17][18][19][20][21][22]. Therefore, our goal was to determine the best conditions for carrying out the solvolysis reaction of synthesized dipeptide analogues of

• . The reactions should proceed with high yields, and any byproducts should be easily removeable. Results and Discussion Dipeptide analogues of α- and β-fluorinated aminophosphonates 5 and 7 were obtained from the corresponding ʟ-amino acids [23][24] 1. In the key step of the synthesis fluorine was

Efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates

• Marcin Kaźmierczak and
• Henryk Koroniak

Beilstein J. Org. Chem. 2020, 16, 756–762, doi:10.3762/bjoc.16.69

• Herein, we present an efficient synthesis of dipeptide analogues of α-fluorinated β-aminophosphonates. Each step of the synthesis was optimized to provide excellent yields. Moreover, the absolute configuration of the obtained compounds was determined by X-ray analysis, which proved the stereochemistry

• that was proposed based on NMR studies. Keywords: dipeptide analogues; fluorinated aminophosphonates; fluorine; nucleophilic fluorination; phosphorus; Introduction The chemistry of fluorinated aminophosphonates is constantly being developed, mainly due to their wide spectra of applications. What is

• regioselectivity of the fluorination reaction. The absolute configuration of the obtained compounds was determined and confirmed by X-ray analysis. Furthermore, we present the use of α-fluorinated β-aminophosphonates as building blocks in the synthesis of their dipeptide analogues. In addition, we show the results

Design, synthesis and biological evaluation of immunostimulating mannosylated desmuramyl peptides

• Rosana Ribić,
• Ranko Stojković,
• Lidija Milković,
• Mariastefania Antica,
• Marko Cigler and
• Srđanka Tomić

Beilstein J. Org. Chem. 2019, 15, 1805–1814, doi:10.3762/bjoc.15.174

• and increase of lipophilicity are important approaches in the preparation of muramyl dipeptide analogues with improved pharmacological properties. Mannose receptors present on immunocompetent cells are pattern-recognition receptors and by mannose ligands binding they affect the immune system. Here we