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An N-protection free ligation of the peptide thioester and the peptide with an N-alkoxy- or N-aryloxyamino group at its N-terminus
Tetrahedron Letters ( IF 1.8 ) Pub Date : 2017-10-27 , DOI: 10.1016/j.tetlet.2017.10.074
Hironobu Hojo , Toru Kawakami , Yuta Hiroyama , Saburo Aimoto

Peptides with an N-alkoxy or N-aryloxy amino acid at their N-terminus were synthesized and successfully ligated with a peptide thioester by silver ion activation under a slightly acidic condition without requiring protection of the side chain amino groups. The N-methoxy group was easily cleaved by the SmI2 reduction in CH3OH aq. to obtain the desired peptide with a native peptide bond. This method was successfully applied to the synthesis of the human atrial natriuretic peptide showing the efficiency of the novel ligation.



中文翻译:

肽硫酯和肽在其N端具有N-烷氧基-或N-芳氧基氨基的N保护自由连接

合成了在其N末端具有N-烷氧基或N-芳氧基氨基酸的肽,并通过在弱酸性条件下通过银离子活化成功地将肽硫酯与肽硫酯连接,而无需保护侧链氨基。该Ñ甲氧基组容易被SMI裂解2在CH还原3 OH水溶液。获得具有天然肽键的所需肽。该方法已成功应用于人心房利钠肽的合成,显示了新型连接的效率。

更新日期:2017-10-27
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