[2-(4-Chlorophenyl)sulfonylethoxycarbonyl (Cps) amino-protecting group for the synthesis of peptides in a solution. Synthesis of [Leu]enkephalin and its [D-ala2]analog].
Solution syntheses of [Leu]enkephalin and its [D-Ala2]analogue were accomplished using a new 2-(4-chlorophenyl)sulfonylethoxycarbonyl (Cps) base-labile group for amino protection and a chromogenic acid-labile 4-(4-phenylazo)benzyloxybenzyl (Abz) group for carboxyl protection. The syntheses were performed by stepwise attachment of Cps-amino acids, which were introduced as pentachlorophenyl esters or as dicyclohexylammonium salts in the presence of tris(dimethylamino)chlorophosphonium perchlorate. To remove Cps-group, Abz-esters of Cps-peptides were treated with two molar equivalents of 1,8-diazabicyclo[5.4.0]undec-7-ene in dimethylformamide followed by neutralization of the base with an excess of 1-hydroxybenzotriazole; the deblocked amino components were then used without isolation. Fully deblocked pentapeptides were purified and characterized by HPLC, FAB mass spectra and amino acid composition.
Sabirov
A N
AN
Ofitserov
V I
VI
Shval'e
A F
AF
Samukov
V V
VV
D000596:Amino Acids; D002264:Carboxylic Acids; D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D004743:Enkephalin, Leucine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D016308:Enkephalin, Leucine-2-Alanine / Q000031:analogs & derivatives*; D007202:Indicators and Reagents; D013058:Mass Spectrometry
D000596:Amino Acids; D002264:Carboxylic Acids; D007202:Indicators and Reagents; D004743:Enkephalin, Leucine; D016308:Enkephalin, Leucine-2-Alanine; C030279:enkephalinamide-Leu, Ala(2)-
2-(4-Khlorfenil)sul'fonilétoksikarbonil'naia (Cps) aminozashchitnaia gruppa dlia sinteza peptidov v rastvore. Sintez [Leu]énkefalina i ego [D-Ala2]analoga.