Efficient and regioselective synthesis of dihydroxy-substituted 2-aminocyclooctane-1-carboxylic acid and its bicyclic derivatives

• İlknur Polat,
• Selçuk Eşsiz,
• Uğur Bozkaya and
• Emine Salamci

Beilstein J. Org. Chem. 2022, 18, 77–85, doi:10.3762/bjoc.18.7

• biological activities, especially applications in the field of medicinal chemistry. β-Amino acids (i.e., amino acids containing an extra methylene group in the backbone) occur naturally in peptidic structures [1][2][3][4][5] and have been used in peptide design to obtain mixed peptides that retain their

Natural and redesigned wasp venom peptides with selective antitumoral activity

• Marcelo D. T. Torres,
• Gislaine P. Andrade,
• Roseli H. Sato,
• Cibele N. Pedron,
• Tania M. Manieri,
• Giselle Cerchiaro,
• Anderson O. Ribeiro,
• Cesar de la Fuente-Nunez and
• Vani X. Oliveira Jr.

Beilstein J. Org. Chem. 2018, 14, 1693–1703, doi:10.3762/bjoc.14.144

• show that both a natural antimicrobial peptide (AMP) derived from wasp venom (decoralin, Dec-NH2), and its synthetic variants generated via peptide design, display potent activity against cancer cells. We tested the derivatives at increasing doses and observed anticancer activity at concentrations as

• of selective anticancer peptide therapeutics. Keywords: breast cancer; decoralin; MCF-7 cells; peptide design; selective anticancer peptides; structure–activity relationships; Introduction Approximately 12% of U.S. women develop breast cancer according to the U.S. Breast Cancer website (http

• investigated Dec-NH2, its LZ template and single/double substituted derivatives for their ability to selectively kill MCF-7 breast cancer cells. Results and Discussion Peptide design, chemical synthesis, purification and physicochemical analyses Dec-NH2 is a cationic α-helical antimicrobial and antiparasitic

Position-dependent impact of hexafluoroleucine and trifluoroisoleucine on protease digestion

• Susanne Huhmann,
• Anne-Katrin Stegemann,
• Kristin Folmert,
• Damian Klemczak,
• Johann Moschner,
• Michelle Kube and
• Beate Koksch

Beilstein J. Org. Chem. 2017, 13, 2869–2882, doi:10.3762/bjoc.13.279

• , and the aspartate protease pepsin. Results and Discussion Peptide design and structure To elucidate the impact of fluorination on proteolytic stability we previously designed the peptide FA (Figure 1b) that comprises the substrate specificities of α-chymotrypsin and pepsin [39][40]. Consequently, the

Molecular architecture with carbohydrate functionalized β-peptides adopting 3₁₄-helical conformation

• Nitin J. Pawar,
• Navdeep S. Sidhu,
• George M. Sheldrick,
• Dilip D. Dhavale and
• Ulf Diederichsen

Beilstein J. Org. Chem. 2014, 10, 948–955, doi:10.3762/bjoc.10.93

• peptide solubility in aqueous solution. Therefore, the β-peptide design provides incorporation of D-glucose, D-galactose and D-xylose derived sugar-β-amino acids at every third position (i and i+3). The remaining positions were filled with β-homolysine and ACHC. For ease of synthesis, β-homoglycine amide

Peptides presenting the binding site of human CD4 for the HIV-1 envelope glycoprotein gp120

• Julia Meier,
• Kristin Kassler,
• Heinrich Sticht and
• Jutta Eichler

Beilstein J. Org. Chem. 2012, 8, 1858–1866, doi:10.3762/bjoc.8.214

• interaction with gp120. Results and Discussion Peptide design and synthesis Based on the resolved 3D structure of the gp120–CD4 complex, we have designed peptides that present the binding site of CD4 for gp120, i.e., residues 22–64 (Table 1). Apart from the peptides covering this complete CD4 stretch (CD4-M1