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In this paper, we describe for the first time the synthesis of new chiral nanosized metal oxide surfaces based on chiral self-assembled monolayers (SAMs) coated with metal oxide (TiO2) nanolayers. In this new type of nanosize chiral surface, the metal oxide nanolayers enable the protection of the chiral self-assembled monolayers while preserving their enantioselective nature. The chiral nature of the SAM/TiO2 films was characterized by variety of unique techniques, such as second-harmonic generation circular dichroism (SHG-CD), quartz crystal microbalance, and chiral adsorption measurements with circular dichroism spectroscopy. The chiral resolution abilities of the SAMs coated with metal oxide (TiO2) nanolayers were investigated in the crystallization of a racemic mixture of threonine and glutamic acid. Our proposed methodology for the preparation of nanoscale chiral surfaces described in this article could open up opportunities in other fields of chemistry, such as chiral catalysis., (Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)