CCL: Chirality assignment test cases

 Sent to CCL by: "Michel PETITJEAN" []
 Dear Mark,
 Simple test cases should appear in stereo nomenclature books (IUPAC,...),
 and the references cited may contain interesting chiral molecules exemplifying
 the rules.
 Inositols, chiral fullerenes, highly bridged graph-symmetric structures,
 non-planar graphs structures, etc., would surely be nice test cases.
 I hope that the CSD contains the connection tables of some of these molecules.
 The "known" chirality is an ambiguous concept: apart in a few simple
 how can we know if the CIP assignment of chirality is possible,
 if not by running some CIP flag assignment program ?
 If the CIP rules are expressed rigorously, the CIP algorithm AND its input data
 must be unambiguous,
 and then the CIP algorithm must be programmable.
 Assuming that the data and the algorithm are defined, the implementation can be
 Invariance of the result upon random renumbering of the connection table is also
 a good test.
 Programming the CIP rules is an exciting project.
 Prelog himself proposed to revise them many years ago.
 I wish you good luck.
 Michel Petitjean
 DSV/iBiTec-S/SB2SM (CNRS URA 2096)
 CEA Saclay, bat. 528
 91191 Gif-sur-Yvette Cedex, France.
 Phone: +331 6908 4006 / Fax: +331 6908 4007
 E-mail: michel.petitjean*|*
 -------- Message d'origine--------
 De: Mark Mackey M.Mackey,+, [mailto:owner-chemistry*|*]
 Date: mer. 01/10/2008 18:42
 Objet : CCL: Chirality assignment test cases
 Hi all.
 I'm testing some old chirality assignment code (using the
 Cahn-Ingold-Prelog rules). It would be really useful if there was a data
 set of test cases with known chirality, ranging from the simple (amino
 acids) right up to the really nasty ones. Does anyone out these have
 such a thing? It's mind-bendingly tedious drawing in and assigning test
 cases by hand...
 Dr Mark Mackey
 Director, Development
 Cresset BioMolecular Discovery Ltd