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首页> 外文期刊>Chemistry: A European journal >Synthesis and membrane binding properties of a lipopeptide fragment from influenza virus a hemagglutinin
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Synthesis and membrane binding properties of a lipopeptide fragment from influenza virus a hemagglutinin

机译：流感病毒血凝素脂肽片段的合成及膜结合特性

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摘要

Hamagglutinin from influenza virus A is a S-palmitoylated lipoglycoprotein in which the lipid groups are thought to influence the interaction between cell membrane and capsid during budding of viral offspring as well as fusion processes of the viral membrane with the endosome after entry of the viral particle into the cell. The paper describes the development of a method for the synthesis of characteristic lipidated hemagglutinin derived peptides which additionally carry the fluorescent 7-nitrobenz-2oxa-1,3-diazole (NBD) group. To achieve this goal the enzyme-sensitive para-phenylacetoxybenzyloxycarbonyl (PAOB) ester was developed. It is cleaved from the peptides and lipidated peptides under very mild conditions and with complete selectivity by treatment with the enzyme penicilin G acylase; this results in the formation of a phenolate. This intermediate spontaneously undergoes fragmentation thereby releasing the desired carboxylates. The combined use of this enzymelabile fragmenting ester with the acid-labile Boc group, the Pd~0-sensitive allyl ester and the corresponding Aloc urethane gave access to a mono-S-palmitolyated and a doubly S-palmitoylated NBD-labelled hemagglutinin peptide. The binding of these lipopeptides to model membranes was analyzed in a biophysical setup monitoring the transfer of fluorescent-labelled lipopeptide from vesicles containing the non-exchangeable fluorescence quencher Rho-DHPE to quencher-free vesicles. The experiments demonstrate that one lipid group is not sufficient for quasi-irreversible membrane insertion of lipidated peptides. This is, however, achieved by introduction of the bis-plamitoyl anchor. The intervesicle transfer always implies release of peptides localized at the outer face of the vesicles intosolution followed by diffusion to and insertion into acceptor vesicles. For peptides bound at the inner face of the vesicle membrane, however, an additional flip-flop diffusion to the outer face has to occur beforehand. The kinetics of these processes were estimated by fast chemical quench of the outside fluorophores by sodium dithionite.
机译：来自流感病毒A的血凝素是一种S-棕榈酰化的脂糖蛋白，其中的脂质基团被认为会影响病毒后代出芽期间以及进入病毒颗粒后病毒膜与内体的融合过程，从而影响细胞膜与衣壳之间的相互作用。进入细胞。本文描述了一种合成特征性脂化血凝素衍生肽的方法的开发，该肽还带有荧光7-硝基苯-2-氧杂-1,3-二唑（NBD）基团。为了实现该目标，开发了对酶敏感的对苯基乙酰氧基苄氧基羰基（PAOB）酯。通过用青霉素G酰基转移酶处理，在非常温和的条件下从肽和脂化的肽上裂解下来;这导致酚盐的形成。该中间体自发地断裂，从而释放出所需的羧酸盐。这种对酶不稳定的片段化酯与对酸不稳定的Boc基团，对Pd〜0敏感的烯丙基酯和相应的Aloc氨基甲酸酯的组合使用，可得到单S-棕榈酰化和双S-棕榈酰化的NBD标记的血凝素肽。这些脂肽与模型膜的结合是在生物物理设置中进行分析的，该装置监测荧光标记的脂肽从含有不可交换的荧光猝灭剂Rho-DHPE的囊泡向无猝灭剂的囊泡的转移。实验表明，一个脂质基团不足以使脂质肽的准不可逆膜插入。然而，这是通过引入双-叶氨酰锚固来实现的。囊泡间转移总是意味着释放位于囊泡外表面的肽释放到溶液中，然后扩散并插入受体囊泡中。然而，对于结合在囊泡膜内表面的肽，必须事先发生额外的触发器扩散到外表面。这些过程的动力学通过连二亚硫酸钠对外部荧光团的快速化学淬灭来估算。

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