Design and synthesis of 4-azido-phosphatidylinositol as a potential probe for metabolic engineering of glycosylphosphatidylinositol on cells

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry Pub Date : 2022-01-01 DOI:10.1080/07328303.2022.2077358

Kendall C. Craig , Zhongwu Guo

引用次数: 2

Abstract

A diacyl phosphatidylinositol (PI) derivative with an azide linked to its inositol C4-position was effectively synthesized in 19 steps for the longest linear sequence and in a ca. 1% overall yield from 1,2-distearoyl-sn-glycerol and D-glucose. This compound was designed as a biosynthetic precursor of glycosylphosphatidylinositol (GPI) anchors. Its azide would enable further modification to introduce other molecular tags by a biocompatible click reaction. Therefore, it can be a useful probe for metabolic engineering of cell surface GPI anchors and GPI-anchored proteins.

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设计与合成4-叠氮-磷脂酰肌醇作为糖基磷脂酰肌醇在细胞上代谢工程的潜在探针

以1,2-二硬脂酰-sn-甘油和d -葡萄糖为原料，通过19步有效地合成了一种二酰基磷脂酰肌醇(PI)衍生物，其叠氮化物与肌醇c4位置相连，具有最长的线性序列，总收率约为1%。该化合物被设计为糖基磷脂酰肌醇(GPI)锚定的生物合成前体。它的叠氮化物可以通过生物相容性点击反应进一步修饰引入其他分子标签。因此，它可以作为细胞表面GPI锚定物和GPI锚定蛋白代谢工程的有用探针。下载:下载高清图片(26KB)下载:下载全尺寸图片

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来源期刊

Journal of Carbohydrate Chemistry 化学-生化与分子生物学

CiteScore

2.10

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Carbohydrate Chemistry serves as an international forum for research advances involving the chemistry and biology of carbohydrates. The following aspects are considered to fall within the scope of this journal: -novel synthetic methods involving carbohydrates, oligosaccharides, and glycoconjugates- the use of chemical methods to address aspects of glycobiology- spectroscopic and crystallographic structure studies of carbohydrates- computational and molecular modeling studies- physicochemical studies involving carbohydrates and the chemistry and biochemistry of carbohydrate polymers.