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一种偶氮苯氨基酸作为多肽中光可切换转向元件的合成与应用。

Synthesis and application of an azobenzene amino acid as a light-switchable turn element in polypeptides.

作者信息

Aemissegger Andreas, Hilvert Donald

机构信息

Laboratory of Organic Chemistry, ETH Zurich, CH-8093 Zurich, Switzerland.

出版信息

Nat Protoc. 2007;2(1):161-7. doi: 10.1038/nprot.2006.488.

Abstract

The synthesis of an azobenzene amino acid (aa) for use as a photo-inducible conformational switch in polypeptides is described. The compound can be easily incorporated into an aa sequence by solid-phase peptide synthesis using standard 9-fluorenylmethoxycarbonyl methods. A reversible conformational change of the peptide backbone is induced by switching between the cis and trans configurations of the azobenzene moiety by irradiation with light of suitable wavelength. Thermal cis --> trans isomerization of this azobenzene aa is slow, enabling detailed structural investigations of the modified peptides, e.g., using NMR techniques. The total time for the synthesis of the photoswitch is typically 4 d, with an overall yield of 40-50%.

摘要

描述了一种用作多肽中光诱导构象开关的偶氮苯氨基酸(aa)的合成方法。该化合物可通过使用标准的9-芴甲氧羰基方法进行固相肽合成,轻松地掺入aa序列中。通过用合适波长的光照射,偶氮苯部分在顺式和反式构型之间切换,从而诱导肽主链发生可逆的构象变化。这种偶氮苯氨基酸的热顺式→反式异构化很慢,这使得能够对修饰后的肽进行详细的结构研究,例如使用核磁共振技术。光开关的合成总时间通常为4天,总产率为40-50%。

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