Readily available amino acid building blocks for the synthesis of phosphole-containing peptides

Biomimetic peptide-based models of [FeFe]-hydrogenases: utilization of phosphine-containing peptides

“…Anhydrous solvents were purchased from Sigma-Aldrich, deuterated solvents from Cambridge Isotope Laboratories, and Fmoc protected amino acids and peptide coupling reagents from Protein Technologies. The compounds 3-(diphenylphosphino)-propionic acid, 21 N-Boc-3-iodo-alanine methyl ester, 22 N-Boc-3-(diphenylphosphorothioyl)-alanine (Boc-Ppa-OH), 14b (μ-pdt)Fe 2 (CO) 6 , 23 and (μ-bdt)Fe 2 (CO) 6 24 were synthesized using literature procedures. The other N-Boc protected phosphine-sulfide amino acids (Boc-Epa-OH and Boc-Ipa-OH) were synthesized by slight modification of the literature method.…”

Phosphorus-containing amino acids with a P–C bond in the side chain or a P–O, P–S or P–N bond: from synthesis to applications

“…Aer the removal of the metal excess, iodoalanine 122 was added to the anion and the tertiary phosphole was trapped with sulfur, leading to the corresponding 3,4-dimethylphospholyl sulde amino ester 125 with 92% yield (Scheme 32). 41 However, under these experimental conditions, where iodoalanine was in the presence of phospholide anion excess, racemization at the a-carbon position couldn't be excluded.…”

Recent Developments in the Synthesis of Amino Acids and Analogues for Foldamers Study

“…A class of phosphorus containing amino acid analogues have been derived by Zutphen and co-workers (Scheme 27) [79]. Starting with N-Boc protected serine 138, the acid was protected selectively using MeI.…”

“…Reagents and conditions: (a) benzene, rt, 24 h; (b) Zn (6 mol equiv), AcOH, rt, 24 h; Phosphole amino acids according to Zutphen et al[79]. Reagents and conditions: (a) MeI, KHCO3 in DMF; (b) PPh3, I2, imidazole in CH2Cl2 for 3.5 h at 0°C; (c) Li-3,4-dimethylphosphole, then S8 in THF.…”