Premium
Glycolide deuteriation by hydrogen isotope exchange using the HSCIE method
Author(s) -
Dos Santos Isabelle,
Morgat JeanLouis,
Vert Michel
Publication year - 1999
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/(sici)1099-1344(199911)42:11<1093::aid-jlcr265>3.0.co;2-0
Subject(s) - chemistry , deuterium , hydrogen–deuterium exchange , polymer , isotope , hydrogen isotope , hydrogen , solid state , radiochemistry , catalysis , molecule , combinatorial chemistry , polymer chemistry , organic chemistry , nuclear physics , physics
Although poly(α‐hydroxy acids)s derived from lactic and glycolic acids (PLAGA) are currently used for many surgical and pharmacological applications, their behaviour and their fate in vivo are still a source of concern according to some authors. As part of our attempts to label these polymers and monitor their fate by using radioactivity, investigation was made of the possibility to exchange the protons present in glycolide molecules by hydrogen isotopes using the High‐temperature Solid‐state Catalytic Isotope Exchange (HSCIE) method which was previously successful in the case of lactide. Accordingly 1 1 H→ 2 1 H exchanges were carried out on glycolide in the presence of Pd/CaCO 3 at various temperatures and 550 mbar pressure of deuterium. Substitution yields as high as 24% were obtained, depending primarily on temperature. PLAGA polymers with lactyl and glycolyl repeating units labeled with deuterium were synthesized and characterized. Copyright © 1999 John Wiley & Sons, Ltd.