Synthesis of α- and β-Substituted Aminoethane Sulfonamide Arginine-Glycine Mimics

An efficient and facile synthesis of N-Cbz-β-aminoalkanesulfonamides

“…Inversely, there is still growing interest in -aminoalkanesulfonamides due to the fact that they can be considered as stable mimetics of tetrahedral transition states in hydrolysis and formation of esters and amides [2]. Therefore, they have been widely used as enzyme inhibitors [3,4], antibacterial [57] and anticancer agents [8]. Additionally, N-protected -aminoalkanesulfonamides as useful building blocks have been successfully employed in the synthesis of sulfonopeptides [1] and hybrid sulfonophosphinopeptides [9,10].…”

“…Alternatively, they were prepared via the direct reaction of aminoalkanesulfonyl chlorides with ammonia or amines [1416]. Aminoalkanesulfinyl chlorides were generally prepared from naturally occurring amino acids or amino alcohols via conversion of them into the corresponding thiolacetates and subsequent treatment with sulfuryl chloride in the presence of acetic anhydride [4,11] or chlorine in an aqueous solution [12,13], or prepared from cysteamine hydrochloride via the oxidation reaction with iodine to the corresponding disulfide, followed by treatment with chlorine in an aqueous solution [1315]. Aminoalkanesulfonyl chlorides can be prepared via oxidation of thiols, thioacetates, or disulfides with phosgene [16,17], triphosgene [18,19], or chlorine in an aqueous solution [15,20], or via reaction of -aminoalkanesulfonic acids or -aminoalkanesulfonates with phosgene [21,22] or triphosgene [23], thionyl chloride [9,24,25], or oxalyl chloride [9,26].…”

Facile synthesis of hybrid sulfonophosphinodipeptides composing of taurines and 1-aminoalkylphosphinic acids

“…Sulfonopeptides have been generally prepared from the reaction of N-protected aminoalkanesulfonyl chlorides with amino acid esters or peptide esters (Xu 2003;Lowik and Liskamp 2000;Gennari et al 1994) or from the condensation of N-protected aminoalkanesulfinyl chlorides and amino esters or peptide esters, followed by subsequent oxidation (Xu 2003;Moree et al 1993Moree et al , 1995. Recently, some sulfino amino acid derivatives, considered as mimetics of sulfonopeptides, have been synthesized (Kukhar et al 2009;Sorochinsky and Soloshonok 2010).…”

A General Route to the Synthesis of N-Protected 1-Substituted and 1,2-Disubstituted Taurines

“…2-Substituted taurines have been synthesized effectively from b-amino primary alcohols, [9][10][11][12][13][14][15][16][17][18] which were easily obtained by reduction of natural amino acids, from b-amino secondary alcohols 19,20 via sulfite displacement of their methanesulfonates, [9][10][11][12] peroxy acid oxidation of their thioacetates, [13][14][15][16][17]21 and sulfite ringopening of aziridines. 18 But little attention has been paid to the synthesis of 1-substituted and 1,2-disubstituted taurines 15,21,22 and their sulfonopeptides. 21,23,24 To synthesize structurally diverse sulfonopeptides, it is very impor-tant to develop an effective and general method for the preparation of 1-substituted and 1,2-disubstituted taurines.…”

“…18 But little attention has been paid to the synthesis of 1-substituted and 1,2-disubstituted taurines 15,21,22 and their sulfonopeptides. 21,23,24 To synthesize structurally diverse sulfonopeptides, it is very impor-tant to develop an effective and general method for the preparation of 1-substituted and 1,2-disubstituted taurines. Herein we describe a general route to 1-substituted and 1,2-disubstituted taurines from olefins and epoxides.…”