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Research Interests

The research program in our group integrates organic chemistry, chemical biology, medicinal chemistry and materials chemistry. A special emphasis is placed on training and research in carbohydrate synthesis and on the utilization of this expertise in addressing problems of medicinal and biochemical significance.

    i.       Carbohydrate chemistry

   ii.       Glycopeptide and glycoprotein synthesis

  iii.       Glycobiology

  iv.       Antimicrobial Research

   v.       Synthetic methods and natural products

  vi.       Functional materials

 

Positions Available

Research Fellow positions in organic synthesis

We are seeking highly motivated individuals to work in emerging areas of organic synthesis. The positions involves synthetic methods and target molecule synthesis. Training in carbohydrate synthesis or peptide/protein is a plus. Interested candidates should send a summary of research experience, resume and names of three references to Prof LIU Xuewei (xuewei@ntu.edu.sg).

 

PhD Scholarships in organic chemistry, medicinal chemistry, carbohydrate synthesis, peptide/protein synthesis and glycobiology

Self-motivated individuals are welcome to join us to work in the area of carbohydrate synthesis, glycoprotein synthesis, natural product synthesis, and glycobiology. Candidates should apply through Division website.

 

Selected Publications (1 paper is selected from each year of 2011-2016)

1. Hua Chai, Kim Le Mai Hoang, Minh Duy Vu, Kalyan Pasunooti, Chuan-Fa Liu and Xue-Wei Liu#, “N-Linked Glycosyl Auxiliary-Mediated Native Chemical Ligation on Aspartic Acid: Application towards N-Glycopeptide Synthesis”, Angew. Chem. Int. Ed., 2016, 55, 10363-10367. Highlighted by X-MOL.

2. Shaohua Xiang, Kim Le Mai Hoang, Jingxi He, Yujia Tan and Xue-Wei Liu#, “Reversing the Stereoselectivity of a Palladium-Catalyzed O-Glycosylation through an Inner-Sphere or Outer-Sphere Pathway”, Angew. Chem. Int. Ed., 2015, 54, 604-607.

3. Kim Le Mai Hoang and Xue-Wei Liu#, “The Intriguing Dual-Directing Effect of 2-Cyanobenzyl Ether for Highly Stereospecific Glycosylation Reaction”, Nat. Commun., 2014, 5, 5051.

4. Jing Zeng, Jimei Ma, Shaohua Xiang, Shuting Cai, and Xue-Wei Liu#, “Stereoselective β-C-Glycosylation via Palladium-Catalyzed Decarboxylative Allylation: Formal Synthesis of Aspergillide A”, Angew. Chem. Int. Ed., 2013, 52, 5134-5137. Highlight in Synfacts 2013, 9, 870.

5. Bala Kishan Gorityala, Zhiqiang Lu, Min Li Leow, Jimei Ma, and Xue-Wei Liu#, “Design of a “Turn-off/Turn-on” Biosensor: Understanding Carbohydrate-lectin Interactions to Utilization in Noncovalent Drug Delivery”, J. Am. Chem. Soc., 2012, 134, 15229-15232.

6. Rujee Lorpitthaya, Sharad B. Suryawanshi, Siming Wang, Kalyan Kumar Pasunooti, Shuting Cai, Jimei Ma, and Xue-Wei Liu#, “Total Synthesis of Sialic Acids by a Sequential Rhodium-Catalyzed Azridination and Barbier Allylation of D-Glycal, Angew. Chem. Int. Ed., 2011, 50, 12054-12057.

 

Selected projects

a)  Acceptor-controlled Glycosylation and Carbohydrate Synthesis

i)    Hydrogen-bonding mediated glycosylation

Figure 1: Dual-directing effect of 2-cyano benzyl ether group on stereospecific glycosylation

Results were published: Kim Le Mai Hoang and Xue-Wei Liu#, Nat. Commun., 2014, 5, 5051. Notably, we received very encouraging and positive comments from reviewer: “Current principles in carbohydrate synthesis such as neighbour group participation, H-bonding, intramolecular aglycone delivery, solvent effect, and arming-disarming strategy are elegantly united in this work.”

ii)   Palladium mediated glycosylation

Figure 2: Reversing stereoselectivity via inner sphere or outer sphere pathway

Results were published: Shaohua Xiang, Kim Le Mai Hoang, Jingxi He, Yujia Tan and Xue-Wei Liu#, Angew. Chem. Int. Ed., 2015, 54, 604-607.

b)  Dual Native Chemical Ligation (dNCL) and Complex Protein Synthesis

i)    Asp-based dual native chemical ligation and glycoprotein synthesis

Results were published: Hua Chai, Kim Le Mai Hoang, Minh Duy Vu, Kalyan Pasunooti, Chuan-Fa Liu and Xue-Wei Liu#, Angew. Chem. Int. Ed., 2016, 55, 10363-10367. Highlighted by X-MOL. Singapore “Provisional” patent application was filed on 18 March 2016 (Ref: PAT/293/15/16/SG PRV).

Figure 3: Quick assembly of homogeneous glycoproteins and glycopeptides via asp-based dNCL

ii)   Lys-based dual native chemical ligation and di-ubiquitin synthesis

Results were published: 1) Kalyan Kumar Pasunooti, Renliang Yang, Seenuvasan Vedachalam, Bala Kishan Gorityala, Chuan-Fa Liu and Xue-Wei Liu#, Bioorg. Med. Chem. Lett., 2009, 19, 6268-6271; 2) Renliang Yang, Kalyan Kumar Pasunooti, Fupeng Li, Xue-Wei Liu# and Chuan-Fa Liu#, J. Am. Chem. Soc., 2009, 131, 13592-13593. This work was highlighted twice by Chemical & Engineering News (C&EN, Sept. 21, 2009; and Nov. 16, 2009): “By moving the thiol handle just one carbon down the lysine side chain, to the γ position, researchers in Singapore could direct two ligations for the price of one. Using their γ-thiol modified lysine, Xue-Wei Liu, Chuan-Fa Liu and coworkers at Nanyang Technological University successfully placed a ubiquitin tag on a 12-amino-acid peptide.

Results were published: Renliang Yang, Kalyan Kumar Pasunooti, Fupeng Li, Xue-Wei Liu# and Chuan-Fa Liu#, Chem. Commun., 2010, 46, 7199-7201. This work was highlighted by Chemical & Engineering News (C&EN, Oct. 11, 2010, PP36-37). It was also selected for Chemical Year in Review (C&EN, Dec. 20, 2010, PP13-17).

 

Figure 4: Quick assembly of branching peptides and di-ubiquitin via Lys-based dNCL

Figure 5: Lys-based dual native chemical ligation highlighted by Chemical Engineering News.

c)  Glycobiology: Exploring and Exploiting Carbohydrate-Lectin Interactions

i)    “Turn off/turn on” biosensor

Figure 6: “Turn-off” and “turn-on” system to probe carbohydrate-lectin interactions

Results were published: 1) Bala K. Gorityala, Zhiqiang Lu, Min Li Leow, Jimei Ma, Xue-Wei Liu#, J. Am. Chem. Soc., 2012, 134, 15229-15232; 2) Xumeng Wu, Yu Jia Tan, Hui Ting Toh, Lan Huong Nguyen, Shu Hui Kho, Sing Yian Chew, Ho Sup Yoon and Xue-Wei Liu#, Chem. Sci., 2016, under revision; 3) Patent application, 61/871,508, NTU Ref: PAT/150/13/13/US PRV.

ii)   Cell secretion biosensor

Figure 7: Glycosylated nanotubes interfacing living cells to detect neuron-type cell secretion

Results were published: 1) Herry Gunadi Sudibya, Jimei Ma, Xiaochen Dong, Simon Ng, Lain-Jong Li, Xue-Wei Liu# and Peng Chen#, Angew. Chem. Int. Ed., 2009, 48, 2723-2726; 2) Jimei Ma, Yanying Zhao, Simon Ng, Jing Zhang, Jing Zeng, Aunt Than, Peng Chen, and Xue-Wei Liu#, Chem. Eur. J., 2010, 16, 4533-4540; 3) Bala Kishan Gorityala, Jimei Ma, Xin Wang, Peng Chen and Xue-Wei Liu,# Chem. Soc. Rev., 2010, 39, 2925-2934.

d)  Sugar-oriented Synthesis of Natural Products and Drugs

Figure 8: Concise synthesis of natural products and drugs starting from D-glucal

Many results have been published in top journals: 1) Jing Zeng, Jimei Ma, Shaohua Xiang, Shuting Cai and Xue-Wei Liu#, Angew. Chem. Int. Ed., 2013, 52, 5134-5137; Highlight in SYNFACTS 2013, 9, 870; 2) Jing Zeng, Yu Jia Tan, Jimei Ma, Min Li Leow, Davin Tirtorahardjo and Xue-Wei Liu#, Chem. Eur. J., 2014, 20, 405-409; 3) Ronny William, Siming Wang, Feiqing Ding, Elise Nerissa Arviana and Xue-Wei Liu#, Angew. Chem. Int. Ed., 2014, 53, 10742-10746; 4) Rujee Lorpitthaya, Sharad B. Suryawanshi, Siming Wang, Kalyan Kumar Pasunooti, Shuting Cai, Jimei Ma and Xue-Wei Liu#, Angew. Chem. Int. Ed., 2011, 50, 12054-12057; etc.

 

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