Chirality reversal between enantiomers is of great importance in both fundamental science and practical applications in chiroptics, biomedicine, and analytical chemistry. Here, we demonstrate an abrupt sign reversal of circular dichroism (CD) between artificial plasmonic diastereoisomers, which are a kind of stereo twisted metamolecules with different strength of deformations. The sign of the CD response is reversed in the same wavelength region by simply engineering the deformation height of nanostructures. Electromagnetic multipolar analysis shows that the sign of CD is determined by the phase-controlled handedness-dependent excitations of electric quadrupole modes. The numerical simulations are further verified by experiments using a nano-kirigami fabrication method. This work reveals that under certain circumstances, the CD response of the plasmonic diastereoisomers can be very close to that of enantiomers, which is useful for the exploration of profound chiroptics, as well as for the applications in chirality switching, chiral biosensing, and chiral separation.