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Synlett 2000; 2000(12): 1708-1720
DOI: 10.1055/s-2000-8669
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Acyl Phosphate Esters: Charge-Directed Acylation and Artificial Blood

Ronald Kluger*
  • *Department of Chemistry, University of Toronto, Toronto, Canada M5S 3H6; E-mail: rkluger@chem.utoronto.ca
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Publication Date:
31 December 2000 (online)

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Acyl phosphate monoesters are water-stable anionic electrophiles that react efficiently with amines to form amides. Some of these are key intermediates in biochemical processes that involve acylation. The anionic reagents are attracted to positively charged sites, promoting site-selective reactions. Multifunctional versions can be used to make rigid, site-defined cross-links in hemoglobin, producing oxygen-carrying alternatives to red cells for transfusions. Direct, efficient synthetic routes to these and related reagents should lead to their wider use.

acylations - regioselectivity - nucleophilic additions - amides - proteins