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@ARTICLE{Klika:136951,
      author       = {K. Klika$^*$ and A. Wzorek and V. A. Soloshonok},
      title        = {{I}nternal chirality descriptors i{R} and i{S} and ire and
                      isi. {A} proposed notation to extend the usefulness of the
                      {R}/{S} system by retaining the sense of stereochemistry in
                      cases of ligand ranking changes.},
      journal      = {Chirality},
      volume       = {30},
      number       = {9},
      issn         = {0899-0042},
      address      = {New York, NY [u.a.]},
      publisher    = {Wiley Interscience},
      reportid     = {DKFZ-2018-01380},
      pages        = {1054 - 1066},
      year         = {2018},
      abstract     = {The R/S system, universally applied for indicating the
                      absolute configuration of a structure, is extremely adept
                      for conveying the absolute configuration unequivocally.
                      However, it suffers from one limitation, viz that due to CIP
                      priority rules the rankings of the ligands attached to an
                      asymmetric center can be altered upon a change in a ligand
                      leading to a change in the designated configuration even if
                      bonds to the asymmetric center were not actually formed or
                      broken. This means that the sense of stereochemistry in
                      situations such as within a set of compounds where family
                      relationships are of focus or where the sense of the
                      stereochemical course of a reaction is of interest can be
                      lost or confusion may occur. This shortcoming is easily
                      remedied though by defining a fixed ranking for a particular
                      ligand in the system under study, eg, the ligand at which
                      the change has occurred. The configurations are then
                      expressed as iR or iS, akin to the R and S descriptors, for
                      sp3 -hybridized tetrahedral chiral structures and similarly,
                      as ire and isi faces, akin to the re and si descriptors, for
                      sp2 -hybridized trigonal prochiral structures. All in all,
                      the notation can be considered as an auxiliary to extend the
                      usefulness of the R/S system. Thus, the proposed iR/iS
                      notation could find profitable use in comparative studies
                      where there is a need to avoid confusion arising from
                      changing assignments due to priority rules or to expedite
                      the ease of comprehension. Moreover, in the current digital
                      age, the facile retrieval of stereochemically clear data by
                      machines is highly desirable-something that the iR/iS
                      notation is readily amenable to.},
      cin          = {G404},
      ddc          = {570},
      cid          = {I:(DE-He78)G404-20160331},
      pnm          = {317 - Translational cancer research (POF3-317)},
      pid          = {G:(DE-HGF)POF3-317},
      typ          = {PUB:(DE-HGF)16},
      pubmed       = {pmid:29978505},
      doi          = {10.1002/chir.22982},
      url          = {https://inrepo02.dkfz.de/record/136951},
}