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E u r o S c i C o n C o n f e r e n c e o n
Chemistry
2018
Chemistry 2018
Journal of Organic & Inorganic Chemistry
ISSN 2472-1123
F e b r u a r y 1 9 - 2 0 , 2 0 1 8
P a r i s , F r a n c e
Page 41
Biocatalysis has emerged as an elegant and green tool for modern organic
synthesis due to its high efficiency, good selectivity and environmental
acceptability. Although, an enzyme is capable of catalyzing a specific reaction
effectively, some unexpected experimental results have indicated that many
enzymes are catalytically promiscuous. Mimetic peptides based on enzyme
as a kind of important chiral scaffold are broadly identified for their obvious
advantages, diverse structures and readily accessibility. Based on promiscuous
aldo-keto-reductase enzymes, several mimetic peptides were designed which
were synthesized and tested as multifunctional organocatalysts in direct
asymmetric aldol and Michael reactions. The asymmetric aldol and Michael
reactions, as the most prominent carbon-carbon bond formation reactions,
are the central study issues in the field of asymmetric synthesis. In this study,
promiscuous aldo-ketoreductase (AKR) is used to catalyze aldol reaction
between aromatic aldehydes and ketones. Good yield (up to 75%), moderate
enantioselectivity (60%), and high diastereoselectivity (dr) up to 93/7(anti/syn)
were obtained. Several mimetic peptides from AKR’s active site were designed
and synthesized as asymmetric catalysts in the aldol and Michael reactions.
The corresponding aldol products were produced with high yields (up to 97%)
and excellent diastereoselectivities (up to 99/1) and enantioselectivities (up
to 99.9) under mild reaction conditions. These peptides exhibit excellent
catalytic activity in terms of yield, diastereoselectivity and enantioselectivity.
The secondary structures of peptide catalysts provide an understanding of
their mechanism.
Biography
Saadi Bayat received his BSc in Applied Chemistry at Buali Sina
University (Hamedan, Iran, 2000). He did his MSc in Organic
Chemistry at Kharazmi University (Tehran, Iran, 2008). Later he
enrolled for the PhD programme at Department of Chemistry,
Faculty of Science of University of Putra Malaysia (UPM), under
the supervision of Prof. Dr. Mohd Basyaruddin Abdul Rahman.
The following year, he was offered scholarship from Graduate
Research Assistance (GRA), UPM. Moreover, his research pro-
gram focuses on mimetic peptide as asymmetric catalysis. He
was as a Postdoctoral Research Fellow for a year (May 2014-
June. 2015) in UPM. He had been selected to receive Endeav-
or Scholarship from the Australian government and joined Dr.
Bellinda Abott’s group in La Trobe University, Melbourne (July
2015-January 2016). He has published almost 20 papers and
has been serving as an Editorial Board Member in journals of
repute.
Mimetic peptides based on promiscuous enzyme as asymmetric catalyst in
aldol and Michael reactions
Saadi Bayat1, 2 and Basyaruddin A Rahman1
1Universiti Putra Malaysia, Malaysia
2Tofigh Daru, Pharmaceutical Company, Iran
Saadi Bayat, J Org Inorg Chem 2018, Volume: 4
DOI: 10.21767/2472-1123-C1-002