Infrastructure | Scientific-research Laboratories

R&d laboratory of heterocyclic amino acids synthesis
R&D Laboratory of «Heterocyclic amino acids» was found in 2009 at the Department of Chemistry, Chair of Pharmaceutical Chemistry

Field – Bioorganic Chemistry


Main directions of research

To develop productive methods for the asymmetric synthesis of optically active (S)- and (R)-a-amino acids of various nature and structure with heterocyclic radicals, to synthesize new heterocycle substituted amino acids, to study and clarify their structure and absolute configuration and to investigate their antimicrobial and other properties.

  • Development of NiII square-planar complexes as model systems of pyridoxalphosphate- dependent enzymes.,
  • Development of asymmetric synthesis methods for new optically active (S)- and (R)-a-amino acids containing heterocyclic rings in the side chain radical.,
  • Development of asymmetric synthesis methods for (S)- and (R)-a-amino acids containing acetylene bonds in the side chain radical.


Modernity


Biomimetic asymmetric synthesis is one of the effective approaches to the synthesis of chiral analogues of natural metabolites. Non-protein amino acids as non-reversible inhibitors of enzymes are also among such compounds. They have both a wide range of physiological activity and are of special interest in modern pharmacy, medicine, microbiology, as well as in other fields of science and technology. Nowadays there are a number of antitumor, antiviral, antihypertensive and other drug preparations, pharmaceutically active aglycone of which is considered as a non-protein amino acid or a peptide composed of non-protein amino acid. Besides, the contribution of non-protein amino acids in biological and biochemical research paves the way to discover a new series of biopreparations. Heterocycle substituted

a-amino acids of non-protein nature are very important, being foreign for the organism by both structure, and heteroatoms nature. In pharmacy a great deal of interest can be provoked by optically active a-amino acids with acetylene bond in the side chain radical, as they are active inhibitors of different enzymes. It is worth to mention that the number of heterocycle substituted amino acids described in literature is strictly limited, they are known as optically inactive racemate mixtures. The direction of enantiomerically pure heterocycle substituted amino acids synthesis has been successfully developed at the Department of Pharmaceutical Chemistry since 2000. Dozens of new heterocycle substituted (S)- and (R)-a-amino acids have already been synthesized. Therefore, the urgent issue of nowadays is the development of efficient methods for the asymmetric synthesis of optically active a-amino acids containing new various heterocyclic and acetylene bonds in the side chain radical.


Goals and Objectives

In the framework of the project it is foreseen to carry out the following studies:

  • to synthesize new effective amino acid and dehydroamino acid synthons, complexes of modified and non-modified chiral auxiliaries, amino acids (including propargylglycine), as well as NiII square-planar complexes of the Schiff`s bases of dehydroamino acids,
  • to study asymmetric condensation reactions of heterocyclic electrophilic agents with amino acid complexes generating enantiomerically enriched a-heterocycle substituted (S)- and (R)-a-amino acids, correspondingly,
  • to study asymmetric addition reactions of heterocyclic nucleophilic agents with dehydroamino acid complexes generating enantiomerically enriched β-heterocycle substituted (S)- and (R)-a-amino acids, correspondingly,
  • to study condensation reaction of alkyl halogenides of various structure with acetylenic moiety of propargylglycine complex under CuI catalysis condition (Sonogashira reaction) isolating new optically pure amino acids containing acetylene bond in the side chain radical,
  • to synthesize heterocycle a- and β-substituted (S)- and (R)-a-amino acids samples of various structure, as well as with acetylene bonds in the side chain radical, to study and clarify their chemical structure and absolute configuration, as well as to study antimicrobial and biological properties of those synthesized samples.



Technical equipment

Department of Chemistry, Chair of Pharmaceutical Chemistry of YSU has the following equipment for the noted studies:

  • melting point determination device,
  • rotary evaporators,
  • magnetic stirrers,
  • electronic scales,
  • vacuum desiccator,
  • analytical balance,
  • water distillation device,
  • polarimeter,
  • flask heaters,
  • vacuum pumps,
  • ultraviolet lamp,
  • water pump,
  • mechanical stirrer

 

International cooperation, grants

The following grant projects were and are being realized by the R&D lab staff:
  • 2000-2012 grants ISTC #A-56; ISTC #A-683; ISTC #2780; ISTC #A-1247; ISTC #CI-073; ISTC #A-1677,
  • 2010-2011 grant ECSP-09-93-SASP,
  • 2012-2014 Armenian-German VolkswagenStiftung grant lD Az 86 223,
  • 2012-2013 Armenian-French grant IE-034,
  • 2013-2015 Armenian-Russian grant 13RF-054,
  • 2013-2014 grant YSSP-13-40


Scientific adviser of R&D laboratory
Ashot S. Saghyan, DSc, Professor, Academician of NAS RA


Laboratory staff

Arpine V. Geolchanyan, PhD in Chemistry, senior researcher,
Satenik Gh. Petrosyan, PhD in Chemistry, senior researcher,
Anahit M. Hovhannisyan, PhD in Biology, senior researcher,
Anna F. Mkrtchyan, PhD in Chemistry, researcher,
Hayarpi M. Simonyan, PhD in Chemistry, researcher



Tel.: (+374 60) 710411; (inner line 34-11)
Fax: (+374 10) 559355
E-mail: saghyan@ysu.am
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