A new method for the solution and solid phase synthesis of chiral β-sulfonopeptides under mild conditions

Synthesis, Conformational Studies and Binding Properties of Acyclic Receptors for N-Protected Amino Acids and Dipeptides

“…The unchanged amino groups on the resin were capped with acetylimidazole (AcIm). Deprotection of the Fmoc groups and treatment with the -valine-derived β-NFmoc-aminosulfonyl chloride 8, with DMAP as catalyst and methyl trimethylsilyl dimethylketene acetal (MTDA) as HCl scavenger, [14,17] gave the bis(sulfonamide) 10. Two cycles were required to ensure completion of the coupling, until no free amino groups could be detected by two different colour tests.…”

Synthesis of Chiral Vinylogous Sulfonamidopeptides (vs-Peptides)

“…Synthesis of Ͱ,β-Unsaturated Sulfonates (6) (S)-N-BocϪvsAlaϪOMe (6, R 1 ϭ Me): Following the above procedure but using methyl (diethylphosphoryl )methanesulfonate, the desired product was obtained in 75% yield after flash chromatography (n-hexane/ethyl acetate, 75:25) and crystallization (n-hexane/ethyl acetate, 7: H 7.22, N 5.28; found C 45.21, H 7.28, N 5.25.…”

“…[6] The conformational preferences of chiral vinylogous amino sulfonic acids (vs-amino acids) and of the corresponding oligomers 3 (vs-peptides) [7] were recently investigated by a combination of X-ray crystallography, variable temperature (VT) 1 H-NMR spectroscopy, FT-IR spectroscopy, and n.O.e. experiments.…”

The first synthesis of optically active 1-substituted taurines

“…1-Substituted 2-aminoethanesulfonic acids (1-substituted taurines) and 2-substituted 2-aminoethanesulfonic acids (2-substituted taurines) are two types of structural analogues of naturally occurring amino acids for β-aminoalkanesulfonic acids. Optically active 2-substituted taurines have been synthesized effectively from optically active β-amino primary alcohols [3,[7][8][9][10][11][12][13][14][15][16], which were easily obtained by reduction of natural amino acids, via sulfite displacement of their methanesulfonates [7][8][9][10], or peroxy acid oxidation of their thioacetates [11][12][13][14][15], and sulfite ring opening of optically active aziridines [16]. But little attention has been paid to synthesis of 1-substituted taurines [13,[17][18][19].…”