LAM Yulin

LAM Yulin

Associate Professor

LAM Yulin

Personal Web Page

Research Fellow, Institute of Molecular and Cell Biology, 1994-1996; Research Fellow, The Scripps Research Institute, 1992-1994; Ph.D., National University of Singapore, 1992; B.Sc. (Hons), National University of Singapore, 1987.

Contact Information:

Office: S8-05-09

Tel: (65)-6516-2688

Fax: (65)-6779-1691

Email: chmlamyl@nus.edu.sg

Research

ORCID: 0000-0003-0984-9492

ResearcherID: B-1755-2018

 

Research Interests

Our research interests include (i) bioorganic and medicinal chemistry, and (ii) green chemical synthesis. Specific foci are:

 

Research Highlight

Ref: Glycosaminoglycans (GAGs) regulate many important physiological processes. A pertinent issue to address is whether GAGs encode important functional information via introduction of position specific sulfate groups in the GAG structure. However, procurement of pure, homogenous GAG motifs to probe the “sulfation code” is a challenging task due to isolation difficulty and structural complexity. To this end, we devised a divergent synthetic strategy to obtain all the 16 theoretically possible sulfation patterns in the chondroitin sulfate (CS) repeating unit; these include rare but potentially important sulfated motifs which have not been isolated earlier.

Molecular recognition of different CS analogues is achieved via surface-enhanced Raman scattering spectroscopy and by inducing charge and geometry complementarity between 4-mercaptopyridine probe and the CS isomers. By “locking” each CS in a unique complex geometry via site-specific, multidentate interactions, our platform mimics molecular docking events to enable high spectral specificity and multiplex quantification. (Angew. Chem. Int. Ed. 2023, e202309610).

Ref: Amide bond formation reaction is one of the most frequently performed reactions in organic chemistry research laboratories, and industrially it is commonplace in polymer, chemical, agrochemical and pharmaceutical production. In view of its relevance, a plethora of strategies to generate the amide bond from alkene, alkynes, carbonyl compounds and other functional groups have been reported. Despite these developments, the direct condensation of carboxylic acids and amines in the presence of stoichiometric quantities of coupling reagents remains the most frequently employed approach to amide bond formation. However this process leads to the generation of large quantities of waste making it nonoptimal from the perspective of atom economy and cost effectiveness. To mitigate this issue, we have developed a thermally stable, fluorous sulfur-containing boronic acid which is able to efficiently promote dehydrative condensation between carboxylic acids and aminds under environmentally friendly conditions. The methodology can be applied to aliphatic, aromatic and heteroaromatic acids as wells as primary and secondary amines. N-Boc protected amino acids were also successfully coupled in good yileds with very little racemization. The catalyst could be reused four times with no significant loss of activity. (RSC Adv. 2023, 13 17420).

 

Teaching Contributions AY2023/2024

 

Representative Publications