[Dmt1]DALDA, SUPER-DALDA
Chemical Name: 2,6-Dimethyl-L-tyrosyl-D-arginyl-L-phenylalanyl-L-lysinamide
项目整合开发状态: Preclinical
项目研究机构: AstraZeneca (Originator)
合成路线:The title peptide was prepared by solid-phase synthesis using a p-methylbenzhydrylamine resin (II).Coupling of Boc-lysine(2-ClZ) (I) to the resin (II) using diisopropylcarbodiimide (DIC) and 1-hydroxybenzotriazole (HOBt) afforded the amide resin (III).The N-Boc group was then selectively deprotected with trifluoroacetic acid in CH2Cl2,yielding resin (IV).To this were sequentially attached the protected amino acids: Boc-phenylalanine (V),Boc-D-arginine(Ts) (VII) and Boc-2',6'-dimethyltyrosine(Boc) (IX) employing DIC/HOBt and then Boc deprotection with trifluoroacetic acid to provide the peptide resins (VI),(VIII) and (X),respectively.Finally,the desired peptide amide was deprotected and cleaved from the resin (X) by treatment with HF and anisole.
📌 参考资料/链接：
参考文献标题:DALDA analogs and their use
文献作者:Schiller,P.(AstraZeneca AB)
参考来源:WO 0055189
📄 详细内容
合成路线:The title peptide was prepared by solid-phase synthesis using a p-methylbenzhydrylamine resin (II).Coupling of Boc-lysine(2-ClZ) (I) to the resin (II) using diisopropylcarbodiimide (DIC) and 1-hydroxybenzotriazole (HOBt) afforded the amide resin (III).The N-Boc group was then selectively deprotected with trifluoroacetic acid in CH2Cl2,yielding resin (IV).To this were sequentially attached the protected amino acids: Boc-phenylalanine (V),Boc-D-arginine(Ts) (VII) and Boc-2',6'-dimethyltyrosine(Boc) (IX) employing DIC/HOBt and then Boc deprotection with trifluoroacetic acid to provide the peptide resins (VI),(VIII) and (X),respectively.Finally,the desired peptide amide was deprotected and cleaved from the resin (X) by treatment with HF and anisole.
参考文献标题:Synthesis and in vitro opioid activity profiles of DALDA analogues
文献作者:Schiller,P.W.; Nguyen,T.M.-D.; Berezowska,I.; Dupuis,S.; Weltrowska,G.; Chung,N.N.; Lemieux,C.
参考来源:Eur J Med Chem 2000,35(10),895