Acyline

D-阿拉尼胺,N-乙酰-3-(2-萘基)-D-丙烯基-4-氯-D-苯丙二酰-3-(3-吡啶基)-D-丙烯酰-L-丝基-4-(乙酰氨基)-L-苯丙酰-4-(乙酰氨基)-D-苯丙酰-L-白基-N6-(1-甲基乙基)-L-赖基-脯氨酰-Chemical Name: Acetyl-2-naphthyl-D-alanyl-4-chloro-D-phenylalanyl-3-pyridyl-D-alanyl-L-seryl-4-acetamido-L-phenylalanyl-4-acetamido-D-phenylalanyl-L-leucyl-Nepsilon-isopropyl-L-lysyl-L-prolyl-D-alaninamide
CAS No. 170157-13-8
项目整合开发状态: Phase I
项目研究机构: Salk Institute for Biological Studies (Originator), University of Washington (Originator)
合成路线:The title compound was obtained by solid-phase peptide synthesis using a methylbenzhydrylamine resin.After attachment of N-Boc-D-alanine (I) to the resin by means of diisopropylcarbodiimide (DIC),the N-Boc protecting group was cleaved by treatment with a solution of trifluoroacetic in CH2Cl2 in the presence of 1,2-ethanedithiol,yielding the alanine-bound resin (II).To this were sequentially coupled the appropriate protected amino acids using DIC,each followed by the Boc group cleavage with trifluoroacetic acid.Coupling/deprotection cycles with N-Boc-L-proline (III),N-alpha-Boc-N-epsilon-benzyloxycarbonyl-N-epsilon-isopropyl-L-lysine (V),N-Boc-L-leucine (VII),N-alpha-Boc-N-4-Fmoc-L-4-aminophenylalanine (IX),N-alpha-Boc-N-4-Fmoc-D-4-aminophenylalanine (XI) and N-Boc-O-benzyl-L-serine (XIII),furnished the peptide resins (IV),(VI),(VIII),(X),(XII) and (XIV).

合成路线:Coupling/deprotection cycles with N-Boc-D-(3-pyridyl)alanine (XV),N-Boc-D-4-chlorophenylalanine (XVII) and N-Boc-D-(2-naphthyl)alanine (XIX) furnished the peptide resins (XVI),(XVIII) and (XX).

合成路线:The side-chain Fmoc protecting groups of (XX) were then cleaved by treatment with piperidine in DMF,and the resulting compound (XXI) was acetylated with acetic anhydride to give (XXII).Finally,removal of the remaining protecting groups and cleavage from the resin was achieved by treatment with liquid HF and anisole.