LaaMII

Chemical Name: N-(2-Aminododecanoyl)-glycyl-L-cysteinyl-L-cysteinyl-L-seryl-L-asparaginyl-L-prolyl-L-valyl-L-cysteinyl-L-histidyl-L-leucyl-L-glutamyl-L-histidyl-L-seryl-L-asparaginyl-L-leucyl-L-cysteine cyclic S-3.2-S-3.8:S-3.3-S-3.16-bis(disulfide)
项目整合开发状态: Biological Testing
项目研究机构: University of Queensland (Originator)
合成路线:Alkylation of diethyl acetamidomalonate (I) with 1-bromodecane (II) affords malonate (III).Subsequent hydrolysis and decarboxylation of (III) under acidic conditions leads to 2-aminododecanoic acid (IV).This is then protected as the N-Boc derivative (V) upon treatment with Boc2O and NaOH

合成路线:The protected peptide-bound resin (VI) is prepared by solid-phase synthesis on a p-methylbenzhydrylamine resin,using HBTU/DIEA activation.Coupling of 2-(Boc-amino)dodecanoic acid (V) to the peptide resin (VI) by means of HBTU affords amide (VII).The DNP protecting groups of the histidine residues of (VII) are subsequently removed by treatment with 2-mercaptoethanol to provide (VIII).Further acidic cleavage of the N-terminal Boc group of (VIII) with trifluoroacetic acid leads to resin (IX).The linear peptide (X) is then cleaved from the resin by treatment with liquid (HF) in the presence of p-thiocresol

合成路线:Finally,air oxidation of the linear peptide (X) in a dilute solution of ammonium bicarbonate at pH 8 furnishes the desired bis-disulfide compound