[p-Sulfotetrafluorophenyl hydrophilic activated esters of amino acids in peptide synthesis].
Highly reactive hydrophilic (i.e., water-soluble) p-sulfotetrafluorophenyl esters (Tfs esters) are proposed for peptide synthesis in aqueous and aqueous-organic media, as well as for protein and peptide partial synthesis in an aqueous medium. These esters can serve as a basis for creating a series of protein modifying reagents. As they are analogs of the widely used pentafluorophenyl esters, the Tfs esters possess a high reactivity coupled with good stability during storage. The expression for the reaction rate (for substrates AA1 and AA2) is shown to be v = k[Boc-AA1-OTfs][H-AA2-NH2]0.5 for both water and DMF, i.e., the reaction is not a simple second-order reaction. The reaction rate in water is only slightly lower than that in DMF.
Medvedkin
V N
VN
Zabolotskikh
V F
VF
Permiakov
E A
EA
Mitin
Iu V
IuV
Sorokina
M N
MN
Klimenko
L V
LV
D000596:Amino Acids / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry; D007202:Indicators and Reagents; D007700:Kinetics; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D013463:Sulfuric Acid Esters / Q000737:chemistry*
D000596:Amino Acids; D007202:Indicators and Reagents; D010455:Peptides; D013463:Sulfuric Acid Esters; D005461:Fluorine