Representation of Molecular Configurations by CAST Coding Method

A configurational CAST (CAnonical representation of STereochemistry) coding method, which represents relative and absolute configuration, is described. The configurational CAST codes are constructed by canonical rotation of the dihedral angles of the input structure before the CAST codes are assigned. Using the configurational CAST, configurational differences can be distinguished independently of conformational differences. Representation of enantiomers is also achieved by a mirror image conversion method. The CAST representation shows the distinctive characteristics of several diastereomers and conformers that were examined. The method clearly represents the differences in configurations. Applications to organic molecules having complex stereochemistry are also demonstrated.

[1]  W. T. Wipke,et al.  Stereochemically unique naming algorithm , 1974 .

[2]  W. T. Wipke,et al.  Computer graphics determination and display of stereoisomers in coordination compounds , 1978 .

[3]  IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). Conformational nomenclature for five and six-membered ring forms of monosaccharides and their derivatives: recommendations 1980. , 1980, European journal of biochemistry.

[4]  J. E. Leonard,et al.  CANONICAL NUMBERING, STEREOCHEMICAL DESCRIPTORS, AND UNIQUE LINEAR NOTATIONS FOR POLYHEDRAL CLUSTERS , 1983 .

[5]  Kazuo Tanaka,et al.  A convenient notation system for organic structure on the basis of connectivity stack , 1984, J. Chem. Inf. Comput. Sci..

[6]  T. Akutsu.  A New Method of Computer Representation of Stereochemistry. Transforming a Stereochemical Structure into a Graph. , 1991 .

[7]  H. Koshino,et al.  Reveromycins, new inhibitors of eukaryotic cell growth. III. Structures of reveromycins A, B, C and D. , 1992, The Journal of antibiotics.

[8]  M. Ubukata,et al.  Absolute configuration of reveromycin A, an inhibitor of the signal transduction of epidermal growth factor , 1994 .

[9]  K. Wüthrich,et al.  Recommendations for the presentation of NMR structures of proteins and nucleic acids – IUPAC-IUBMB-IUPAB Inter-Union Task Group on the Standardization of Data Bases of Protein and Nucleic Acid Structures Determined by NMR Spectroscopy , 1998, European journal of biochemistry.

[10]  E. Theodorakis,et al.  Enantioselective Total Synthesis of Reveromycin B. , 1999 .

[11]  A. Cuzzupe,et al.  Total synthesis of (-)-reveromycin B. , 2004, Organic letters.

[12]  E. Theodorakis,et al.  Stereoselective total synthesis of reveromycin B and C19-epi-reveromycin B. , 2000, Chemistry.

[13]  K. Funatsu,et al.  Novel Canonical Coding Method for Representation of Three‐Dimensional Structures. , 2000 .