Below we list individual references and links to the respective publisher web sites for each of the "new" rules available in the Tautomerizer. The prototropic rules PT_02_00 through PT_21_00 are the standard tautomeric transforms implemented in the chemoinformatics toolkit CACTVS, predominantly describing well-known types of tautomerism such as keto-enol tautomerism, for which we are therefore not providing separate evidence from literature.
Based on Baldwin’s Rules1 , which estimate the likelihood of ring closure reactions to occur, our group previously developed a set of transforms (RC_01_00 to RC_11_00) covering the majority of ring–chain tautomerism cases2.  Some of these rules have more than one variant (such as RC_05_00 to RC_05_04), yielding a total of 38 SMIRKS transforms. From among these rules, we have included those few transforms in the Tautomerizer that cover the well-known sugar ring-chain tautomerism (RC_03_00 and RC_04_01).

  1. Baldwin, J.E. Rules for Ring Closure. J. Chem. Soc., Chem. Commun., 1976, 734-736. Link
  2. Guasch, L., Sitzmann, M., & Nicklaus, M. C. (2014). Enumeration of Ring–Chain Tautomers Based on SMIRKS Rules. J. Chem. Inf. Model., 54(9), 2423-2432. Link

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Last Update: 2020-01-10