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26296-50-4

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From plant to probe: Semi-synthesis of labelled undecaprenol analogues allows rapid access to probes for antibiotic targets
Undecaprenol-containing glycolipids (UCGs) are essential precursors of bacterial glycopolymers and glycoproteins. We report a novel semi-synthetic strategy to prepare labelled UCGs directly from undecaprenol. This one-size-fits-all approach offers a concise and efficient method for obtaining labelled-UCGs, which will allow new mechanistic studies and inhibitor screens to be performed on novel antibiotic targets.
Alexander, Francesca M.,Boland, Coilín,Caffrey, Martin,Cochrane, Rachel V. K.,Cochrane, Stephen A.,Fetics, Susan K.
supporting information
p. 8603 - 8606
(2020/08/21)

Synthesis of undecaprenyl pyrophosphate-linked glycans as donor substrates for bacterial protein N-glycosylation
Synthesis of undecaprenyl pyrophosphate (Und-PP)-linked glycans is described. Bacterial ([E]3,[Z]7)-undecaprenol was synthesized from trans-geranylgeranyl sulfone and isoprenoid building blocks, which was converted to undecaprenyl ph
Lee, Yong Joo,Ishiwata, Akihiro,Ito, Yukishige
experimental part
p. 6310 - 6319
(2009/12/06)

BIOSYNTHESIS OF A D-GLUCOSYL POLYISOPRENYL DIPHOSPHATE IN PARTICULATE PREPARATIONS OF MICROCOCCUS LYSODEIKTICUS
Particulate fractions of Micrococcus lysodeikticus incubated with UDP-D-glucose incorporated radioactivity into a chloroform-methanol-soluble, low-mol. wt. compound, and into a polymer.The low-mol. wt. compound consisted of a glucolipid that was extremely labile to mild acid hydrolysis with the formation of D-glucose, and to mild alkali, yielding 14C-labeled α-D-glucopyranose 1,2-phosphate and D-glucose 2-phosphate.The labeled glucolipid was eluted from a DEAE-cellulose column at a salt concentration higher than that required by synthetic ficaprenyl (D-glucopyranosyl phosphate), and it migrated more slowly than the latter compound in t.l.c.Formation of glucolipid was stimulated by exogenous ficaprenyl phosphate, but not by C55-dolichyl phophate.These results suggest that the glucolipid has the characteristic properties of a polyisoprenyl glucosyl diphosphate.
Yamazaki, Tatsumi,Laske, Douglas W.,Herscovics, Annette,Warren, Christopher D.,Jeanloz, Roger W.
p. 159 - 170
(2007/10/02)

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Chemical Properties

Boiling Point: 777.0±29.0 °C(Predicted)
Density: 0.890±0.06 g/cm3(Predicted)
PKA: 14.42±0.10(Predicted)
PSA: 20.23000
LogP: 18.20990

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