Synthesis of novel d-α-galactopyranosyl-l-seryl/l-threonyl-l-alanyl-l-alanine as useful precursors of new glycopeptide antibiotics with computational calculations studies. (April 2022)

• Record Type: Journal Article
• Authors: Khodair, Ahmed I.; Kassab, Shaymaa E.; Kheder, Nabila A.; Fahim, Asmaa M.
• Is Part Of: Carbohydrate research. Volume 514(2022)
• Publication Date: 2022-04
• Subjects: N-Boc-protected amino acids esters -- Peptide mimetic -- Glycopeptide derivatives -- Theoretical investigation; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2022.108546
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: New, simple, synthetic routes for the preparation of novel glycopeptide antibiotics are described. The structures of the synthesized compounds are elucidated by IR, two-dimensional NMR spectroscopy, and mass spectrometry. The stability of the new glycopeptide derivatives 10a, b is confirmed by assessing the physical character, HOMO-LUMO gap energy, ESP, and the corresponding correlation of 2D-NMR analysis. Furtherly, the target precursors are investigated via the DFT/B3LYP/6–311(G) basis set. Graphical abstract: Image 1 Highlights: Synthesis of novel d -α-Galactopyranosyl-L-seryl/L-threonyl-L-alanyl-l - alanine. Elucidation of obtained glycosides via DFQ and HMQC (2D NMR). Optimization of synthesized d -galactopyranosyl utilized DFT/B3LYP/6–31(G) basis set. NMR correlation of glycopeptide 10a, 10b and confirmed via experimental data.