Synthesis of mannose 6-phosphonates (isosteric analogues of mannose 6-phosphates)

Authors
Vidil, C Vidal, S Morere, A Montero, JL
Citation
C. Vidil et al., Synthesis of mannose 6-phosphonates (isosteric analogues of mannose 6-phosphates), PHOSPHOR SU, 158, 2000, pp. 125-139
Citations number
15
Categorie Soggetti
Inorganic & Nuclear Chemistry
Journal title
PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
ISSN journal
10426507 → ACNP
Volume
158
Year of publication
2000
Pages
125 - 139
Database
ISI
SICI code
1042-6507(2000)158:<125:SOM6(A>2.0.ZU;2-T
Abstract
The synthesis of two isosteric phosphonate analogs of the M6P recognition m arker, present in the lysosomal enzyme structure, is described. The phospho nate 1, a bioisosteric analog of the M6P was obtained via a multistep synth esis using the trimethylsilyl protective group. Only this method allowed th e obtention of the mannosylphosphonate 2, functionalized in the anomeric po sition by a paraaminophenyl group which is commonly use to link proteins or other substrates of biological interest.