Antimicrobial resistance is a major global health threat, with fungal pathogens increasingly causing untreatable infections. Among these, Candida albicans stands out as a particularly urgent concern due to its prevalence, adaptability, and rising resistance to antifungal drugs. Systemic infections caused by this pathogen can lead to serious illness and even death, especially in immunocompromised individuals. This thesis explores multifunctional glycoconjugates designed not only to block C. albicans virulence but also to enable its detection using advanced diagnostic platforms. The central hypothesis is that targeting fungal adhesion, a key virulence factor, can disrupt colonization without exerting lethal pressure, thereby reducing the risk of resistance development. Chapter 1 discusses the synthesis of a library of aromatic core glycoconjugates (AGCs) featuring divalent triazolyl β-galactoside motifs with different aromatic substituents, aiming to disrupt C. albicans adherence to host cells. This structure-activity relationship study revealed that lipophilic aromatic substituents with moderate steric bulk enhance anti-adhesion activity, while computational analysis confirmed that active AGCs adopt stable conformations favourable for enhanced anti-adhesion ability. Selected AGCs from this study which incorporated electrophilic warheads (vinyl sulfone, acrylamide), were examined for their covalent crosslinking capabilities with nucleophilic amino acids and demonstrated fungicidal activity, showcasing the first covalent glycoconjugates targeting fungal pathogens. A further collaborative study also demonstrated the replacement of the aromatic core with heterocycles coordinated to metal centres improved activity. To extend their functionality, novel AGCs were conjugated to multivalent platforms such as fluorescent carbon dots (CDs), gold nanoparticles (AuNPs), and microplastic (MP) beads, creating dual-purpose probes for therapeutic and diagnostic applications. Chapter 3 describes the synthesis and successful conjugation of complex carbohydrates to CDs, which effectively inhibited fungal adhesion and demonstrated the utility of multivalent platforms. Chapter 4 presents the synthesis and characterisation of Raman-active AuNP glycoprobes for a proof-of-concept detection method using Surface Enhanced Raman Spectroscopy (SERS) and Broadband Coherent Anti-Stokes Raman Spectroscopy (BCARS). These probes also enabled rapid colorimetric detection of C. albicans via surface plasmon resonance shifts. To improve on the detection method MP-based glycoprobes were synthesised to enhance signal clarity, reducing background interference, and enabling future multiplexed pathogen detection. Collectively, this work establishes a platform that combines anti-virulence therapy with next-generation diagnostics. By leveraging adhesion inhibition and multivalent glycan presentation, these probes offer a resistance-resilient strategy for managing fungal infections. Integration with advanced spectroscopic and nanoparticle technologies paves the way for rapid, sensitive, and multiplexed detection, with potential applications in clinical diagnostics, environmental monitoring, and antifungal drug development.