Algorithm for exhaustive and nonredundant organic stereoisomer generation.
Generation of organic stereoisomers with R/S, Z/E, and/or M/P configurations that may contain heteroatoms, multiple bonds, and any kind of cycle (isolated, spiro, condensed, and nested) is described. Inputs for processing are molecular structures in a N_tuple format resident on an automatic (canonical) or manual (non canonical) generated file which are processed by doing internal molecular graph construction, a weighted bipartite tree construction for all atoms and bonds to detect stereocenters, and symmetrical atom groups (SAG) with some specific SAG parameters that constitute a novel way for redundancy elimination of meso structures. Finally, determination of ligand CIP priorities allows for writing the output N_tuples with stereoisomer description. Several examples showing application of this methology to a wide number of structures are also presented.
Contreras
M L
ML
Faculty of Chemistry and Biology, Department of Chemical Sciences, University of Santiago de Chile, Casilla 40, Santiago-33, Chile. lcontrer@usach.cl
Alvarez
J
J
Guajardo
D
D
Rozas
R
R
D000465:Algorithms; D002625:Chemistry, Organic / Q000379:methods*; D003201:Computers; D048088:Informatics / Q000379:methods*; D008024:Ligands; D008956:Models, Chemical; D015233:Models, Statistical; D015394:Molecular Structure; D011381:Programming Languages; D020033:Protein Isoforms; D012984:Software; D013237:Stereoisomerism
D008024:Ligands; D020033:Protein Isoforms