Solid phase synthesis without repetitive acidolysis. Preparation of leucyl-alanyl-glycyl-valine using 9-fluorenylmethyloxycarbonylamino acids.
Solid phase synthesis without repetitive acidolysis. Preparation of leucyl-alanyl-glycyl-valine using 9-fluorenylmethyloxycarbonylamino acids.
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固相合成，无需重复酸解。
DOI：
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发表时间：
2009
期刊：
影响因子：
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通讯作者：
C. D. Chang
中科院分区：
文献类型：
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作者：
J. Meienhofer;M. Waki;E. Heimer;T. Lambros;R. Makofske;C. D. Chang
在固相肽合成中，α-氨基保护基的重复非水解碱裂解的实用性通过在对苄氧基苄基酯聚苯乙烯-1%二乙烯基苯树脂载体上制备模型四肽亮氨酰-丙氨酰-甘氨酰-缬氨酸来显示。N α-9-芴基甲氧基羰基（Fmoc：Carpino & Han，1970，1972）氨基酸通过对称酸酐程序偶联，然后使用二氯甲烷中的50%哌啶裂解Fmoc基团。通过用55%三氟乙酸的二氯甲烷溶液处理，从固体载体上定量除去Fmoc-四肽。以87%的总收率获得均质游离四肽。该方法比目前使用酸解重复α-氨基去封闭的固相方法具有优势。
The utility of repetitive nonhydrolytic base cleavage of alpha-amino protective groups in solid phase peptide synthesis is shown by a preparation of the model tetrapeptide leucyl-alanyl-glycyl-valine on a p-benzyloxybenzyl ester polystyrene--1% divinylbenzene resin support. Nalpha-9-Fluorenylmethyloxycarbonyl (Fmoc: Carpino & Han, 1970, 1972) amino acids were coupled by the symmetrical anhydride procedure, followed by Fmoc group cleavage using 50% piperidine in methylene chloride. Quantitative removal of the Fmoc-tetrapeptide from the solid support was effected by treatment with 55% trifluoroacetic acid in methylene chloride. Homogeneous free tetrapeptide was obtained in 87% overall yield. The procedure is proposed to offer advantages over present solid phase methods which use acidolysis for repetitive alpha-amino group deblocking.