PMX-53, AcF-(OPdChaWR)
(3S,9S,12S,15R,18S)-3-(N-乙酰-L-苯基醛氨基)-15-(环己基甲基)-9-(3-胍基丙基)-12-(1H-吲哚-3-甲基)--1,7,10,13,16-戊酰亚氮基环[16.3.0]二十一n-2,8,11,14,17-戊铛Chemical Name: (3S,9S,12S,15R,18S)-3-(N-Acetyl-L-phenylalanylamino)-15-(cyclohexylmethyl)-9-(3-guanidinopropyl)-12-(1H-indol-3-ylmethyl)--1,7,10,13,16-pentaazabicyclo[16.3.0]heneicosane-2,8,11,14,17-pentaone; N-Acetyl-L-phenylalanyl-L-ornithyl-L-prolyl-3-cyclohexyl-D-alanyl-L-tryptophyl-D-arginine N-5.2-C-1.6-lactam
CAS No. 219639-70-0
项目整合开发状态: Phase II
项目研究机构: Promics (Originator), University of Queensland (Originator)
合成路线:The compound was prepared by solid-phase peptide synthesis on a PAM-resin.Starting from a N(alpha)-Boc-N(gamma)-Tos-L-arginine resin (I),cleavage of the Boc protecting group by means of trifluoroacetic acid provided Arg(Tos)-resin (II).Coupling of (II) with N(alpha)-Boc-L-tryptophan (III) using O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU) and diisopropylethylamine,followed by acid cleavage of the Boc group gave dipeptide resin (IV).This was in turn coupled and deprotected with the following amino acids N-Boc-D-cyclohexylalanine (V),N--Boc-L-proline (VII) and N(alpha)-Boc-N(delta)-Tos-L-ornithine (IX) to furnish the peptide resins (VI),(VIII),(X) and (XII),respectively.
合成路线:The resin (X) was coupled with N-Boc-L-phenylalanine (XI) affording resin (XII).The acetylation of the free amino group,side-chain deprotection and cleavage from the resin (XII) employing liquid HF and p-cresol yielded the linear dipeptide (XIII).This was finally cyclized with benzotriazol-1-yloxytris (dimethylamino)phosphonium hexafluorophosphate (BOP) to produce the title cyclic peptide.
📌 参考资料/链接：
参考文献标题:Cyclic agonists and antagonists of C5a receptors and G protein-coupled receptors
文献作者:Fairlie,D.; Wong,A.; Finch,A.M.; Taylor,S.M.(University of Queensland)
参考来源:EP 1017713; WO 9900406
📄 详细内容
合成路线:The compound was prepared by solid-phase peptide synthesis on a PAM-resin.Starting from a N(alpha)-Boc-N(gamma)-Tos-L-arginine resin (I),cleavage of the Boc protecting group by means of trifluoroacetic acid provided Arg(Tos)-resin (II).Coupling of (II) with N(alpha)-Boc-L-tryptophan (III) using O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU) and diisopropylethylamine,followed by acid cleavage of the Boc group gave dipeptide resin (IV).This was in turn coupled and deprotected with the following amino acids N-Boc-D-cyclohexylalanine (V),N--Boc-L-proline (VII) and N(alpha)-Boc-N(delta)-Tos-L-ornithine (IX) to furnish the peptide resins (VI),(VIII),(X) and (XII),respectively.
合成路线:The resin (X) was coupled with N-Boc-L-phenylalanine (XI) affording resin (XII).The acetylation of the free amino group,side-chain deprotection and cleavage from the resin (XII) employing liquid HF and p-cresol yielded the linear dipeptide (XIII).This was finally cyclized with benzotriazol-1-yloxytris (dimethylamino)phosphonium hexafluorophosphate (BOP) to produce the title cyclic peptide.
参考文献标题:Low-molecular-weight peptidic and cyclic antagonists of the receptor for the complement factor C5a
文献作者:Finch,A.M.; Wong,A.K.; Paczkowski,N.J.; Wadi,S.K.; Craik,D.J.; Fairlie,D.P.; Taylor,S.M.
参考来源:J Med Chem 1999,42(11),1965
合成路线:The compound was prepared by solid-phase peptide synthesis on a PAM-resin.Starting from a N(alpha)-Boc-N(gamma)-Tos-L-arginine resin (I),cleavage of the Boc protecting group by means of trifluoroacetic acid provided Arg(Tos)-resin (II).Coupling of (II) with N(alpha)-Boc-L-tryptophan (III) using O-benzotriazol-1-yl-N,N,N',N'-tetramethyluronium hexafluorophosphate (HBTU) and diisopropylethylamine,followed by acid cleavage of the Boc group gave dipeptide resin (IV).This was in turn coupled and deprotected with the following amino acids N-Boc-D-cyclohexylalanine (V),N--Boc-L-proline (VII) and N(alpha)-Boc-N(delta)-Tos-L-ornithine (IX) to furnish the peptide resins (VI),(VIII),(X) and (XII),respectively.
合成路线:The resin (X) was coupled with N-Boc-L-phenylalanine (XI) affording resin (XII).The acetylation of the free amino group,side-chain deprotection and cleavage from the resin (XII) employing liquid HF and p-cresol yielded the linear dipeptide (XIII).This was finally cyclized with benzotriazol-1-yloxytris (dimethylamino)phosphonium hexafluorophosphate (BOP) to produce the title cyclic peptide.
参考文献标题:Small molecular probes for G-protein-coupled C5a receptors: Conformationally constrained antagonists derived from the C terminus of the human plasma protein C5a
文献作者:Wong,A.K.; Finch,A.M.; Pierens,G.K.; Craik,D.J.; Taylor,S.M.; Fairlie,D.P.
参考来源:J Med Chem 1998,41(18),3417
产品链接: CAS No. 219639-70-0››