Dr Jack Chen

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Senior Lecturer - Chemistry

Email: jack.chen@aut.ac.nz

ORCID: ORCID logo  https://orcid.org/0000-0002-4662-4076

Links to relevant web pages:
www.jchenresearch.wordpress.com/

Qualifications:

BSc(Hons), PhD (University of Auckland)

Biography:

I conducted my PhD at the University of Auckland with Prof. Margaret Brimble, working on the synthesis of spirastrellolide B - a potent protein phosphatase inhibitor with potential anti-cancer properties. I then took up a Postdoctoral Fellow appointment in the same group for 18 months, and was involved in a range of projects including the total synthesis of bioactive molecules from traditional Chinese medicines and a medicinal chemistry project to discover novel telomerase inhibitors. In 2011 I moved to Bristol, UK, for 3 years where I worked with Prof. Varinder Aggarwal developing synthetic methodology involving a novel form of activated allylboron reagents. In 2014 I took up a Postdoctoral Fellowship with Prof. Leonard Prins in Padova, Italy, where I studied the use of gold nanoparticle-based supramolecular systems for chiral catalysis. In July 2016 I joined the staff at the School of Science at AUT.

Teaching Areas:

Organic Chemistry; Chemistry for Drug Discovery; General Chemistry

Research Areas:

•    Organic synthesis and methodology development
•    Green catalysis and sustainable chemistry
•    Functionalised gold nanoparticles for drug delivery
•    Understanding reactions kinetics and mechanism

Current Research Projects:

Sustainable chemistry in water catalysed by multi-functionalised gold nanoparticles

In the current battle against climate change, chemists have an even greater responsibility to conduct chemistry with low environmental impact. This means following green chemistry principles such as utilising catalysis and minimising waste. The proposed project aims to immobilise catalysts onto gold nanoparticles which are water soluble, creating catalysts which are effective in water, and which are easily recyclable. How different immobilisation methods affect the kinetics and mechanisms of different reactions will be studied. Reactions of interest include ester formation driven by phase separation, the kinetic resolution of terminal epoxides and aldol reactions catalysed by proline-based organocatalysts. The immobilisation of multiple catalysts will also enable the development of cascade reaction methodology, another important goal in green and sustainable chemistry.

Project1_Original

Drug targeting and delivery using functionalised gold nanoparticles

The versatility of gold nanoparticles can also be showcased in targeted drug-delivery systems. In this project, the modular nature of these monolayer-covered nanoparticles will be utilised to incorporate both active pharmaceuticals (e.g. doxorubicin, a widely used anti-cancer agent) and targeting ligands (e.g. folic acid) into the same system. This means better targeting of drugs to the site of action. For example, delivery vehicles with bound folic acid molecules are able to target tumour cells which exhibit an overexpression of folate receptors. Gold nanoparticles are also able to absorb low-energy radiation, which can be used to induce drug release only at the site of action. These properties make this nanoparticle-based system especially conducive for the treatment of cancer tumours, where targeted release of drugs means greatly reduced side-effects and greatly improved patient outcomes.
Project2_Original

 

 

 

Publications:

P. Solís Muñana†, G. Ragazzon†, J. Dupont, C. Z.‐J. Ren, L. J. Prins, Jack L.‐Y. Chen. Substrate‐Induced Self‐Assembly of Cooperative Catalysts. Angew. Chem. Int. Ed. 2018, Early View, DOI: 10.1002/anie.201810891 (†denotes equal contribution) link

C. García-Ruiz, Jack L.-Y. Chen, C. Sandford, K. Feeney, P. Lorenzo, G. Berionni, H. Mayr, and V. K. Aggarwal. Stereospecific Allylic Functionalization: The Reactions of Allylboronate Complexes with Electrophiles. J. Am. Chem. Soc. 2017, 139, 15324. link

Jack L.-Y. Chen, S. Maiti, I. Fortunati, C. Ferrante, L. J. Prins. Temporal Control over Transient Chemical Systems using Structurally Diverse Chemical Fuels. Chem. Eur. J. 201723, 11549 (Selected as a Hot Paper by the Editors ). link

F. della Sala, S. Neri, S. Maiti, Jack L.-Y. Chen, L. J. Prins. Transient Self-Assembly of Molecular Nanostructures Driven by Chemical Fuels. Curr. Opin. Biotechnol. 201746, 27-33. link

F. della Sala, Jack L.-Y. Chen, S. Ranallo, D. Badocco, P. Pastore, F. Ricci, L. J. Prins. Reversible Electrochemical Modulation of a Catalytic Nanosystem. Angew. Chem. Int. Ed. 201655, 10737-10740. link

C. Pezzato, Jack L.-Y. Chen, P. Galzerano, M. Salvi, L. J. Prins. Catalytic signal amplification for the discrimination of ATP and ADP using functionalised gold nanoparticles. Org. Biomol. Chem. 201614, 6811. link

Jack L.-Y. Chen, C. Pezzato, P. Scrimin, L. J. Prins, Chiral Nanozymes – Gold Nanoparticle-based Transphosphorylation Catalysts Capable of Enantiomeric Discrimination. Chem. Eur. J. 201622, 7028-7032 (Highlighted with frontispiece cover). link

A. Millan, J. R. Smith, Jack L.-Y. Chen, V. K. Aggarwal, Tandem Allylboration-Prins Reaction for the Rapid Construction of Substituted Tetrahydropyrans: Application to the Total Synthesis of (-)-Clavosolide A. Angew. Chem. Int. Ed. 2016, 55, 2498-2502 (selected as a Hot Paper by the Editors). link

C. Pezzato, S. Maiti, Jack L.-Y. Chen, A. Cazzolaro, C. Gobbo, L. J. Prins, Monolayer protected gold nanoparticles with metal-ion binding sites: functional systems for chemosensing applications. Chem Commun. 2015, 51, 9922-9931. link

Jack L.-Y. Chen, V. K. Aggarwal. Highly Diastereoselective and Enantiospecific Allylation of Ketones and Imines using Borinic Esters: Contiguous Quaternary Stereogenic Centers. Angew. Chem. Int. Ed. 2014, 53, 10992-10996 (designated VIP paper). link

H. M. Geng, L. A. Stubbing, Jack L.-Y. Chen, D. P. Furkert, M. A. Brimble. Synthesis of the Revised Structure of Acortatarin A. Eur. J. Org. Chem. 2014, 6227-6241. link

L. Chausset-Boissarie, K.Ghozati, E. LaBine, Jack L.-Y. Chen, V. K. Aggarwal, C. M. Crudden. Enantiospecific, Regioselective Cross-Coupling Reactions of Secondary Allylic Boronic Esters. Chem. Eur. J. 2013, 19, 17698-17701. link

Jack L.-Y. Chen, H. K. Scott, M. J. Hesse, C. L. Willis, V. K. Aggarwal. Highly Diastereo- and Enantioselective Allylboration of Aldehydes using α‑Substituted Allyl/Crotyl Pinacol Boronic Esters via in Situ Generated Borinic Esters. J. Am. Chem. Soc. 2013, 135, 5316-5319. link

T.-Y. Yuen, Y.-P. Ng, F. C. F. Ip, Jack L.-Y. Chen, D. J. Atkinson, J. Sperry, N. Y. Ip, M. A. Brimble. Telomerase Inhibition Studies of Novel Spiroketal-Containing Rubromycin Derivatives. Aust. J. Chem. 2013, 66, 530-533. link

H. M. Geng, Jack L.-Y. Chen, D. P. Furkert, S. Jiang, M. A. Brimble. A Convergent Synthesis of the 2-Formylpyrrole Spiroketal Natural Product Acortatarin A. Synlett 2012, 23, 855-858. link

D. F. Chorley, Jack L.-Y. Chen, D. P. Furkert, J. Sperry, M. A. Brimble. Total Synthesis of Danshenspiroketallactone. Synlett 2012, 23, 128. link

Jack. L.-Y. Chen, J. Sperry, N. Y. Ip. M. A. Brimble. Natural products targeting telomere maintenance. Med. Chem. Commun. 2011, 2, 229-245. link

Jack L.-Y. Chen, M. A. Brimble. Synthesis of the Bis-Spiroacetal Core of the Antimitotic Agent Spirastrellolide B. J. Org. Chem. 2011, 76, 9417-9428. link

Jack L.-Y. Chen, M. A. Brimble. Synthesis of the bis-spiroacetal C25-C40 moiety of the antimitotic agent spirastrellolide B using a bis-dithiane deprotection/spiroacetalisation sequence. Chem. Commun. 2010, 46, 3967-3969. link