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首页> 外文期刊>Chemistry: A European journal >Chemical Synthesis of Burkholderia Lipid A Modified with Glycosyl Phosphodiester-Linked 4-Amino-4-deoxy-beta-L-arabinose and Its Immunomodulatory Potential
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Chemical Synthesis of Burkholderia Lipid A Modified with Glycosyl Phosphodiester-Linked 4-Amino-4-deoxy-beta-L-arabinose and Its Immunomodulatory Potential

机译：糖基磷酸二酯连接的4-氨基-4-脱氧-β-L-阿拉伯糖修饰的伯克霍尔德氏菌脂质A的化学合成及其免疫调节潜力

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摘要

Modification of the Lipid A phosphates by positively charged appendages is a part of the survival strategy of numerous opportunistic Gram-negative bacteria. The phosphate groups of the cystic fibrosis adapted Burkholderia Lipid A are abundantly esterified by 4-amino-4-deoxy-beta-L-arabinose (beta-L-Ara4N), which imposes resistance to antibiotic treatment and contributes to bacterial virulence. To establish structural features accounting for the unique pro-inflammatory activity of Burkholderia LPS we have synthesised Lipid A substituted by beta-L-Ara4N at the anomeric phosphate and its Ara4N-free counterpart. The double glycosyl phosphodiester was assembled by triazolyl-tris-(pyrrolidinyl) phosphonium-assisted coupling of the beta-L-Ara4N H-phosphonate to a-lactol of beta(1 -> 6) diglucosamine, pentaacylated with (R)-(3)-acyloxyacyl- and Alloc-protected (R)-(3)-hydroxyacyl residues. The intermediate 1,1'-glycosyl-H-phosphonate diester was oxidised in anhydrous conditions to provide, after total deprotection, beta-L-Ara4N-substituted Burkholderia Lipid A. The beta-L-Ara4N modification significantly enhanced the pro-inflammatory innate immune signaling of otherwise non-endotoxic Burkholderia Lipid A.
机译：带正电荷的附件对脂质A磷酸盐的修饰是许多机会性革兰氏阴性细菌生存策略的一部分。适应于囊性纤维化的伯克霍尔德氏菌脂质A的磷酸基团被4-氨基-4-脱氧-β-L-阿拉伯糖（β-L-Ara4N）充分酯化，从而增强了对抗生素治疗的抵抗力并有助于细菌致病性。为了建立解释伯克霍尔德氏菌LPS独特促炎活性的结构特征，我们合成了在异头磷酸酯上被β-L-Ara4N取代的脂质A及其不含Ara4N的对应物。双糖基磷酸二酯通过三唑基-三-（吡咯烷基）phospho辅助的β-L-Ara4NH-膦酸酯与β（1-> 6）二葡糖胺的α-内酯组装而成，并被（R）-（3 ）-酰氧基酰基-和Alloc保护的（R）-（3）-羟基酰基残基。在完全脱保护后，将中间体1,1'-糖基-H-膦酸酯二酯在无水条件下氧化，以提供β-L-Ara4N取代的伯克霍尔德氏菌脂质A。β-L-Ara4N修饰显着增强了先天性促炎性非内毒素性伯克霍尔德氏菌脂质A的免疫信号

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