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Cooperability
| Project leader |
Kirin Srećko |
| Administering organization: |
Ruđer Bošković Institute
Bijenička c. 54, HR-10002 Zagreb, Croatia
Dr. Andrea Moguš-Milanković
E-mail: mogus@irb.hr
phone: ++385-1-4561149
Web: www.irb.hr |
| Partner Institution/Company: |
Chirallica d.o.o., Zagreb and Universty of Western Ontario, London |
| Grant type: |
1A |
| Project title: |
Organometallic and inorganic bioconjugates as potential enantioselective catalysts |
| Project summary: |
In recent years, the catalysis of chemical reactions has an enormous impact in industry, the production of most important chemicals involves a catalytical step. Catalysis is particularly important in the synthesis of chiral compounds, a small amount of a chiral catalyst can produce large quantities of chiral products from prochiral substrates. Asymmetric (enantioselective) catalysis draws its inspiration from nature. Since the lock-and-key specificity of natural systems often results in a limited scope, organic synthesis of natural and non-natural compounds offers a more flexible approach and is complementary to biological synthesis.
Chiral metal complexes are used as homogeneous enantioselective catalysts very frequently. The general importance of the incorporation of the chiral information as close as possible to the coordination sphere of the metal, where the actual catalysis takes place, is widely accepted. Within this project, two independent enantioselective catalytical systems (A) and (B) are proposed, that are governed by the same basic principle. In both A and B the coordination sphere of the catalytically active metal centre is only prochiral. The chiral information is transmitted by "backdoor induction" via hydrogen bonding between distant pedant amino acids. An artificial C2-symmetrical peptide turn structure is formed that controls the chirality of the catalysts coordination sphere. The proposed catalysts are relatively small molecules with molecular weight around 1000 g mol-1 accessible in only a few synthetic steps, the sources of chirality are cheap natural amino acids. |
| Hrvatski sažetak: |
Kataliza kemijskih reakcija ima iznimno veliko značenje u kemijskoj industriji, proizvodnja većine važnih kemikalija uključuje katalizu. Kataliza je posebno važna u sintezi kiralnih spojeva, gdje mala količina kiralnog katalizatora može proizvesti veliku količinu kiralnog produkta iz akiralnog polaznog spoja. Asimetrična (enantioselektivna) sinteza nalazi inspiraciju u prirodi. S obzirom da specifičnost prirodnih sustava po načelu ključa i brave često ima vrlo ograničenu primjenu, organska sinteza prirodnih i neprirodnih spojeva nudi fleksibilniji pristup i komplementarna je biološkoj sintezi.
Kiralni metalni kompleksi se vrlo često koriste u homogenoj enantioselektivnoj katalizi. Općenito je prihvaćeno, da je iznimno važno imati kiralnu informaciju što je moguće bliže koordinacijskoj sferi metala, gdje se odvija kataliza. U okviru ovog projekta, predložena su dva međusobno neovisna katalitička sustava (A) i (B), koji se temelje na istom načelu. U oba sustava, koordinacijska sfera metala je samo prokiralna. Kiralna informacija se prenosi "backdoor indukcijom" putem vodikovih veza između udaljenih aminokiselina. Nastaje C2-simetrična struktura peptidnog okreta, koja kontrolira kiralnost koordinacijske sfere katalizatora. Predloženi katalizatori su relativno male molekule molekulske mase oko 1000 g mol-1, dostupne u nekoliko sintetskih koraka, izvor kiralnosti su jeftine prirodne aminokiseline. |
| Amount requested from UKF: |
1.460.000 HRK |
| Amount of matching funding: |
438.000 HRK |
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