Solid-phase synthesis of protected peptides using new cobalt(III) ammine linkers.
Solid-phase synthesis of protected peptides using new cobalt(III) ammine linkers.
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使用新的钴 (III) 氨胺连接体固相合成受保护的肽。
DOI：
10.1111/j.1399-3011.1993.tb00490.x
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发表时间：
1993
期刊：
影响因子：
--
通讯作者：
Isied,SS
中科院分区：
文献类型：
--
作者：
Arbo,BE;Isied,SS
合成了钴(III)配合物[COL4(4-AMB)O-AA-Boc](CF3SO3)2，其中L4=二乙二胺(EN)2或四胺(NH3)4，4-AMB=4-氨基甲基苯甲酸，并将其作为聚苯乙烯树脂的连接剂，用于固相合成保护肽。将BOC/t-Bu保护的脑啡肽组装在两种不同的Co(III)树脂上，然后通过还原Co(III)中心将其从树脂上切割下来，产率为93-96%。以67-69%的总收率获得了纯化的保护脑啡肽，并用氨基酸分析和核磁共振氢谱对其进行了表征。在Co(En)2-树脂上的逐步合成也用于组装Boc‐Asp(OcHex)‐Arg(Mts)‐Gly‐Asp(OcHex)‐Ala‐Pro‐Lys(2Cl‐Z)‐Gly‐OH，a序列，从α1型胶原蛋白中分离出保护肽，产率为74%，并用氨基酸分析、核磁共振氢谱和液体二次离子质谱仪进行了表征。介绍了合成异构型纯Co(III)锚定配合物的新路线。Co(III)树脂被发现与固相多肽合成中使用的叔丁氧羰基(BOC)和9-荧甲氧基羰基(Fmoc)N-α保护基团策略都是相容的。
Cobalt(III) ammine complexes of the typecis‐[CoL4(4‐AMB)O‐AA‐Boc](CF3SO3)2, where L4= bisethylenediamine (en)2or tetraammine (NH3)4, and 4‐AMB = 4‐(aminomethyl)benzoic acid, have been synthesized and used as linkers to polystyrene resins for solid‐phase synthesis of protected peptides. Boc/t‐Bu‐protected [Leu5]enkephalin was assembled on the two different Co(III) resins, and then cleaved from the resins by reduction of the Co(III) center in 93–96%; yield. HPLC‐purified protected [Leu5]enkephalin was obtained in 67–69% overall yield and characterized by amino acid analysis and1H NMR. Stepwise synthesis on the Co(en)2‐resin was also used in the assembly of Boc‐Asp(OcHex)‐Arg(Mts)‐Gly‐Asp(OcHex)‐Ala‐Pro‐Lys(2Cl‐Z)‐Gly‐OH, a sequence from collagen α1 Type 1. The protected peptide was cleaved from the Co(III) resin in 74% yield, and the HPLC‐purified nonapeptide was characterized by amino acid analysis,1H NMR and liquid secondary‐ion mass spectrometry (LSIMS). New routes are described for the synthesis of isomerically pure Co(III) anchor complexes. The Co(III) resins were found to be compatible with both thetert‐butyloxycarbonyl (Boc) and the 9‐fluorenylmethoxycarbonyl (Fmoc) Nα‐protecting group strategies used in solid‐phase peptide synthesis.