The article discusses the issues of developing the principles of a semantically marked parallel corpus of translations of Chekhov's fiction into German within the framework of the Chekhov Digital project, a digital academic publication of the writer's collected works in TEI (Text Encoding Initiative) format. The parallel corpus project is focused on creating a digital infrastructure for studying the writer's works, allowing researchers to analyze and compare original texts with their translations. Difficulties were identified related to the interpretation of significant elements of the writer's works, the specifics of their translation into German and the semantic markup of translations of fiction, for example, difficulties arose with defining the boundaries and relationships between the elements of semantic markup. Ways to overcome them are proposed, including the use of digital methods and natural language processing technologies. The project uses digital methods and technologies of natural language processing, the standard of digital publication Text Encoding Initiative (TEI). The text markup structure based on the TEI standard makes documents machine-readable, which allows to develop tools for complex semantic information retrieval. The inclusion in the Chekhov Digital project of parallel corpora of translations of A. P. Chekhov's works into different languages makes it possible to expand research tools in the field of translation studies, making it possible to compare texts of translations and originals, detect similarities and differences in vocabulary, grammar, style and cultural references, as well as automate routine research processes, which makes search and analysis much more effective information on large volumes of texts. The results of the project will contribute to the development of the digital humanitarian environment, contributing to the preservation and popularization of the literary heritage of A.P. Chekhov. The creation of a semantically marked parallel corpus of translations will be important for literary critics, linguists and translators, allowing them to study the specifics of translations of Chekhov's works and develop new forms of text analysis and interpretation. The experience gained during the project will be valuable for future research and practical applications, demonstrating the effectiveness of digital technologies in humanitarian research and education.