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J Comput Chem. 2013 Oct 30;34(28):2485-92. doi: 10.1002/jcc.23397. Epub 2013 Aug 2.

Batch tautomer generation with MolTPC.

Author information

1
Center for Bioinformatics, Campus Building E2.1, Saarland University, D-66123 Saarbrücken, Germany.

Abstract

Besides all their conformational degrees of freedom, drug-like molecules and natural products often also undergo tautomeric interconversions. Compared to the huge efforts made in experimental investigation of tautomerism, open and free algorithmic solutions for prototropic tautomer generation are surprisingly rare. The few freely available software packages limit their output to a subset of the possible configurational space by sometimes unwanted prior assumptions and complete neglection of ring-chain tautomerism. Here, we describe an adjustable fully automatic tautomer enumeration approach, which is freely available and also incorporates the detection of ring-chain variants. The algorithm is implemented in the MolTPC framework and accessible on SourceForge.

KEYWORDS:

conformational search space; isomers; ring-chain tautomerism; solvent-dependent equilibria; tautomer enumeration

PMID:
24078443
DOI:
10.1002/jcc.23397
[Indexed for MEDLINE]
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