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农杆菌素 C 是一种 Ti 质粒编码的酶产物,是 D-葡萄糖和蔗糖的 2-O、6-O 连接的磷酸二酯。

Agrocinopine C, a Ti-plasmid-coded enzyme-product, is a 2-O, 6-O linked phosphodiester of D-Glucose and sucrose.

机构信息

School of Agriculture, Food and Wine, University of Adelaide, Waite Research Institute, PMB 1, Glen Osmond, South Australia, 5064, Australia.

School of Agriculture, Food and Wine, University of Adelaide, Waite Research Institute, PMB 1, Glen Osmond, South Australia, 5064, Australia.

出版信息

Phytochemistry. 2022 Feb;194:113013. doi: 10.1016/j.phytochem.2021.113013. Epub 2021 Nov 25.

Abstract

Agrocinopine C is a small molecule found in crown gall tumours induced by pathogenic Agrobacterium radiobacter carrying the tumour-inducing plasmid pTi Bo542. This phosphodiester opine was isolated (at 0.02 g/100 g fresh wt.) from sunflower (Helianthus annuus L.) galls. It is structurally related to agrocinopine A and is a glucose-2-phosphodiester linked to the C6-hydroxy-methyl group of the glucose moiety of sucrose. Sugar-2-phosphates are uncommon in plant tissues, whether transformed by Agrobacterium or not. H and P NMR signal multiplicity indicates five-fold anomeric complexity of agrocinopine C in solution, implying that the permeases taking up these sucrose-phosphodiesters could recognise any one of the five anomers. Data suggests that the open chain aldehyde forms of the 2-phosphorylated opines agrocinopine C and agrocinopine A and the corresponding phosphorylated glucose-2-phosphoramidate component of the antibiotic agrocin 84 play a central role in agrocin's selective toxicity to certain strains of Agrobacterium after uptake via Ti plasmid-encoded permeases.

摘要

农杆菌素 C 是一种在由携带致瘤质粒 pTi Bo542 的致病性根癌农杆菌诱导的冠瘿瘤中发现的小分子。这种磷酸二酯类阿泊啡是从向日葵(Helianthus annuus L.)瘿瘤中分离出来的(0.02 g/100 g 鲜重)。它与农杆菌素 A 结构相关,是葡萄糖-2-磷酸酯与蔗糖葡萄糖部分的 C6-羟甲基相连。糖-2-磷酸酯在植物组织中是否被根癌农杆菌转化都不常见。H 和 P NMR 信号多重性表明农杆菌素 C 在溶液中的五重端基异构复杂性,这意味着吸收这些蔗糖磷酸二酯的透性酶可以识别其中的任何一种端基异构体。数据表明,2-磷酸化阿泊啡农杆菌素 C 和农杆菌素 A 的开链醛形式以及抗生素农杆菌素 84 的相应磷酸化葡萄糖-2-磷酸酰胺成分在通过 Ti 质粒编码的透性酶摄取后,对某些根癌农杆菌菌株的农杆菌素选择性毒性中起着核心作用。

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