Sugar-derived oxazolone pseudotetrapeptide as γ-turn inducer and anion-selective transporter

• Sachin S. Burade,
• Sushil V. Pawar,
• Tanmoy Saha,
• Navanath Kumbhar,
• Amol S. Kotmale,
• Manzoor Ahmad,
• Pinaki Talukdar and
• Dilip D. Dhavale

Beilstein J. Org. Chem. 2019, 15, 2419–2427, doi:10.3762/bjoc.15.234

• and Research, Pune, Pune 411008, India 10.3762/bjoc.15.234 Abstract The intramolecular cyclization of a C-3-tetrasubstituted furanoid sugar amino acid-derived linear tetrapeptide afforded an oxazolone pseudo-peptide with the formation of an oxazole ring at the C-terminus. A conformational study of

• transporter for which an anion–anion antiport mechanism was established. Keywords: ion transport; oxazolone; peptidomimetics; pseudo-peptides; sugar amino acid; Introduction Tetrasubstituted α-amino acid (TAA)-derived peptidomimetics offer well-defined turn structures due to the presence of a

Selected synthetic strategies to cyclophanes

• Sambasivarao Kotha,
• Mukesh E. Shirbhate and
• Gopalkrushna T. Waghule

Beilstein J. Org. Chem. 2015, 11, 1274–1331, doi:10.3762/bjoc.11.142

• ] have reported the synthesis of a glycotriazolophane 309 (carbohydrate–triazole–cyclophane hybrid) from a sugar amino acid via a copper-catalyzed azide-alkyne cycloaddition sequence. An aminosugar acid was identified as a useful building block to generate cyclophanes. Thus, the treatment of 304 with

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

• ; sugar amino acid; Introduction Synthetic biomimetic macromolecules, which are capable to fold into well-defined three-dimensional structures in analogy to natural peptides and proteins, have been extensively studied to increase the understanding of complex biomolecules [1][2][3]. In this respect, β

• for carbohydrate and peptide chemistry. Therefore, sugar units are introduced by side-chain ligation and labeling strategies on the peptide scaffold or were established by incorporation of sugar-β-amino acids by solid-phase peptide synthesis (SPPS) [36][37]. Sugar amino acid building blocks have

• ). CD spectra of β-glycopeptides 1–8 (c = 20 μM) in triethylammonium acetate buffer (5 mM, pH 7) at various temperatures. Synthesis of sugar-amino acid building blocks 12a and 12b. Synthesis of the galactosyl β-amino acid building block 12c. Supporting Information Supporting Information File 304