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Electrospray ionization tandem mass spectrometric characteristics of hairpin artificial minic polypeptide

✍ Scribed by Yong Ye; Ming-Yu Niu; Qiang Yin; Li-feng Cao; Yu-Fen Zhao

Publisher
John Wiley and Sons
Year
2005
Tongue
English
Weight
79 KB
Volume
40
Category
Article
ISSN
1076-5174

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✦ Synopsis

Electrospray ionization tandem mass spectrometric characteristics of hairpin artificial minic polypeptide

Recently, polyamides containing N-methylpyrrole and N-methylimidazole amino acids have attracted considerable attention from synthetic and biological chemists because they recognize and bind in the minor groove of predetermined DNA sequences with high affinity and specificity. 1 -6 Since these polyamides can permeate living cell membranes, they have the potential to control specific gene expression. 7 -10 Dervan and co-workers have has established that the sequence specificity of the binding depends on the side-byside base pairings in the minor groove of DNA. 11 -13 Antiparallel pairings of Py/Im distinguishes C ž G from G ž C, A ž T and T ž A base pairs; an Im/Py pair targets a G ž C base pair. Py/Py recognizes both A ž T and T ž A base pairs. 11 -14 We synthesized a hairpin polypeptide as a model compound and studied its interaction with DNA.

The compound was comprised of five structural units (shown in Scheme 1), namely tripolyamide, -aminobutyric acid, tripolyamide, 1,6-hexanediamine and histidine containing a Boc group. Two tripolyamide (units 1 and 3) were connected through a -aminobutyric acid, and comprise a hairpin structure. The tripolyamide (unit 3) and histidine containing a Boc group (unit 5) were connected through a 1,6-hexanediamine. In this work, the fragmentation of synthetic polypeptide was investigated using electrospray ionization mass spectrometry (ESI-MS) combined with tandem mass spectrometry (ESI-MS/MS).

The polypeptide was prepared according to the reported procedure. 15 Mass spectra were acquired in the positive ion mode

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