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Synthesis and Biological Activity of Phosphonate Analogs of Mannose 6‐Phosphate (M6P)
Author(s) -
Vidil Carole,
Morère Alain,
Garcia Marcel,
Barragan Véronique,
Hamdaoui Bassou,
Rochefort Henri,
Montero JeanLouis
Publication year - 1999
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/(sici)1099-0690(199902)1999:2<447::aid-ejoc447>3.0.co;2-r
Subject(s) - phosphonate , chemistry , mannose , mannose 6 phosphate , derivative (finance) , stereochemistry , phosphate , aldehyde , receptor , combinatorial chemistry , biochemistry , growth factor , financial economics , economics , catalysis
Two phosphonate analogs of mannose 6‐phosphate (M6P) have been synthesized. The isosteric analog 1 was obtained by a Wittig–Horner reaction at position 6 of a sugar aldehyde. The non‐isosteric analog 2 was obtained by a Michaelis–Arbuzov rearrangement of a 6‐bromo derivative. In contrast to the non‐isosteric analog 2 , the isoster 1 was shown to bind to M6P receptors as effectively as does M6P itself, thus demonstrating the considerable potential of the system in drug design.