Extended CAST Coding Method for Exact Search of Stereochemical Structures

Abstract

Accurate recognition of differences and similarities in stereochemical structures is achieved by extended CAST (CAnonical-representation of STereochemistry) coding method. Using the CAST notations, complete search of partial structures as well as whole structures by matching with the query in any level from a specific atom considering planar, configurational, and conformational information has been achieved. Differences and similarities of stereochemistry in four aldopentoses of D-xylose, D-ribose, D-arabinose, and D-lyxose, which have three chiral centers, are clearly represented by the extended CAST. Applications for some organic compounds containing more complicated stereochemical structures are also demonstrated.

First Total Synthesis of Vialinin A, a Novel and Extremely Potent Inhibitor of TNF-α Production

“…In previous papers, one of us developed a new stereochemical coding method, CAST (CAnonical representation of STereochemistry) and successfully applied it to a database-oriented 13 C NMR chemical shift prediction system, called CAST/CNMR . In the course of studies applying CAST/CNMR to terphenyls, we found that 13 C NMR data of the terminal aromatic rings of 1 were similar to those of ganbajunin C isolated from edible Chinese mushroom, Thelephora ganbajun (Figure ) and felt that the proposed structure 14 was quite strange because two model compounds ( 15 and 16 18 ) exhibited clearly different 13 C NMR spectra (Table ).…”

Structural Revision of Terpenoids with a (3Z)-2-Methyl-3-penten-2-ol Moiety by the Synthesis of (23E)- and (23Z)-Cycloart-23-ene-3β,25-diols

“…and H.S.) developed a new stereochemical coding method, CAST (CAnonical-representation of STereochemistry) [15][16][17] and successfully applied it to a database-oriented 13 C NMR chemical shift prediction system, called CAST/CNMR. [18][19][20] In the course of studies applying CAST/CNMR to cycloart-23-en-25-ol derivatives, we could not find reliable 13 stereochemistry.…”

“…and H.S.) developed a new stereochemical coding method, CAST (CAnonical-representation of STereochemistry) − and successfully applied it to a database-oriented 13 C NMR chemical shift prediction system, called CAST/CNMR. − In the course of studies applying CAST/CNMR to cycloart-23-en-25-ol derivatives, we could not find reliable 13 C NMR data of compounds with the 2-methyl-3-penten-2-ol moiety that possesses Z stereochemistry. − Total synthesis of 1 and 2 also has not been reported. Therefore, we planned to prepare authentic samples to add into the database of CAST/CNMR.…”

G-RMSD: Root Mean Square Deviation Based Method for Three-dimensional Molecular Similarity Determination

“…Thus, the core part of this study is to develop an ecient algorithm to solve this maximization problem eq. (12).…”