TY - JOUR
TI - The use of J-coupling as a sole criterion to assign the total absolute stereochemistry of new pyrrolidinone class synthetic analogs, derived from S-pyroglutamic acid
AU - Kellici, T.F.
AU - Ntountaniotis, D.
AU - Vanioti, M.
AU - Golic Grdadolnik, S.
AU - Simcic, M.
AU - Michas, G.
AU - Moutevelis-Minakakis, P.
AU - Mavromoustakos, T.
JO - Journal of Molecular Structure
PY - 2017
VL - 1129
TODO - null
SP - 195-199
PB - Elsevier B.V.
SN - 0022-2860
TODO - 10.1016/j.molstruc.2016.09.075
TODO - Bioactivity;  Nuclear magnetic resonance spectroscopy;  Organic compounds;  Stereochemistry, Absolute stereochemistry;  Chiral centers;  J coupling;  Pyroglutamic acids;  Pyrrolidinone;  Synthetic analogs, Stereoselectivity
TODO - During the synthesis of new pyrrolidinone analogs possessing biological activity it is intriguing to assign their absolute stereochemistry as it is well known that drug potency is influenced by the stereochemistry. The combination of J-coupling information with theoretical results was used in order to establish their total stereochemistry when the chiral center of the starting material has known absolute stereochemistry. The J-coupling can be used as a sole criterion for novel synthetic analogs to identify the right stereochemistry. This approach is extremely useful especially in the case of analogs whose 2D NOESY spectra cannot provide this information. Few synthetic examples are given to prove the significance of this approach. © 2016 Elsevier B.V.
ER -