This study is devoted to the problems of development of digital resources for education based on use of semantic technologies and knowledge management models aimed at the analysis of educational content. Digital transformation is a complex problem, therefore, we analyze only the semantic representation andsearch of learning objects (LOs) used by andragogue for construction of personalized learning trajectories(PLT). This special case of LO selection takes into account more complex set of their properties andanalyzes both LO metadata standards and elements of domain-specific characteristics of LOs. Proposed approach is aimed on the digital transformation of learning activities based on use of semantic technologies and knowledge management models that support analysis, structuring and retrieval of educational content with use of external knowledge sources. We propose information retrieval system that process formalized knowledge about learning course and student needs to find pertinent LOs that can be used in student PLT. An ontological approach provides creation of learning course thesaurus, and this thesaurus is processed as an input of retrieval procedure. Search results need in additional indexing with use of LO metadata standards and individual estimates of andragogue that transforms information into the LOs. Semantic Wiki environment is used for support of such indexingand storing of retrieved LOs and their structure.