Bio-organic Chemistry and Metabolites

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Dr Sitaram Swain

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Core Courses

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Course Name : Bio-organic Chemistry and Metabolites

Code(Credit) :CUTM1696(3-2-1)

Course Objectives

  • Understand the significance of organic reactions with reference to biological systems. Understanding chemical bonding, strong and weak interactions, hydrogen bonding and to apply these principles in various biomolecules and biological reactions. Understanding the formation of polymers and their importance; difference between biodegradable and non-biodegradable polymers and biohazards of polymers.

Learning Outcomes

  • On completion of this course, students will understand the significance of organic reactions with reference to biological systems, chemical bonding in various biomolecules, strong and weak interactions. They will gain a good understanding of aliphatic and aromatic compounds, IUPAC nomenclature, reactivity of functional groups and the importance of stereoisomers in biological systems.

Course Syllabus

Module:I Introduction to organic chemistry:Classification of organic compounds, unique characteristics, IUPAC nomenclature of organic compounds (including bi-functional) and biomolecules.Reaction mechanisms:Concept of inductive effect, resonance and hyperconjugation.Classification of organic reactions (substitution, addition, elimination and rearrangement), with two examples for each. Concepts of the following – carbanions, carbocations, free radicals, carbenes, nucleophiles and electophiles (Formation and Stability).
Module:II Aliphatic hydrocarbons: Mechanism of Markownikoff and anti-Markownikoff addition. Addition of HBr to propene. Dienes – types with examples, 1,3 butadiene –Preparation, stability and mechanism of addition of HBr. Diels-Alder reaction. Conformational analysis of ethane.
Module:III Cycloalkanes:Reactivity and relative stability. Bayer’s strain theory. Sachse-Mohr theory. Boat and chair forms of cyclohexanes. Axial and equatorial bonds and their relation with biological activities of carbohydrates.
Module: IV Arenes: Structure of benzene – by Resonance and molecular orbital theories. Aromaticity. Mechanism of Nitration and Friedel- craft reaction. Electronic interpretation of the orientating influence of substituents in the electrophilic substitution of toluene, chlorobenzene, nitrobenzene and phenol. Resonance structures of naphthalene and anthracene. Alkyl halides and organomatellic compounds:SN1 and SN2 reaction, their mechanism with one example for each. Concept of elimination reactions (E1 and E2 with an example). Applications of organometallic compounds – organo lead, organo lithium, cis-platin.
Module:V Alcohols:Definition, classification, monohydric alcohols-distinguishing reactions for primary, secondary and tertiary alcohols.Dihydric alcohols: Glycol, preparation (any 2 methods) and uses.Trihydric alcohols: Glycerol, synthesis from propene, properties, (reaction with conc. H2SO4, HNO3, Oxalic acid and HI). Phenols: Acidity of phenols, effect of substituent on acidity.
Hydroxy acids and dicarboxylic acids: Structure & properties ofhydroxy acids: Lactic acid, citric acid and isocitric acid. Dicarboxylic acid: Maleic and fumaric acid. Ketoacids: Pyruvic, α-ketoglutaric, oxalo acetic acids.
Amines: Classification, properties, functional amino group – Basicity of amines, acylation.
React with HNO2& Schiff’s base formation. Distinguishing reactions of primary, secondary and tertiary amines.
Module:VI Heterocyclic compounds: Definition, classification with examples, structure and biological importance of furan, pyrrole, thiophene, pyridine, pyran, thiazole, pyrimidine, purine, indole, imidazole, quinoline and isoquinoline. Basicity of pyrrole and pyridine.
Terpenes: Definition, isoprene rule, classification, isolation, structure and biological importance of menthol, camphor, farnesol, phytol, lanosterol, lycopene and dolichols.
Steroids: Basic ring structure in steroids. Structure and biological importance of cholesterol, phytosterols and ergosterol. Bile acids [Mono, Di & Tri cholic acids].
Alkaloids: Definition, classification based on their structure and biological functions, isolation, structure and biological action of morphine, nicotine & atropine. Chemical synthesis of nicotine and atropine.
Module: VII Vitamins: Classification- Water soluble & fat soluble. Structural formulae and co-enzyme forms of B1, B2, B6 and niacin. Vitamin C as red-ox reagent, Chemical synthesis of vitamin C. Structural formula of vitamin A, D, E and K.
Stereochemistry:Stereoisomerism, types, Fischer-projection formulae, chiral carbon atom, asymmetry and dissymmetry, chirality, conditions for optical isomerism ex: glyceraldehyde, lactic acid, tartaric acid, Nomenclature of enantiomers, diastereomers. D and L notation, R and S system, racemisation and resolution (Biochemical, chemical and physical methods).Geometrical isomerism.
Practical content:
• Systematic qualitative analysis of the organic compounds:Urea, benzamide, benzaldehyde, aniline, acetophenone, m-cresol, nitrobenzene, chlorobenzene, naphthalene, p-toluidine,benzoic acid, salicylic acid, resorcinol, benzyl alcohol and p-dichoro benzene.
• Organicpreparations: Aspirin from salicylic acid, benzoic acid from benzaldehyde, p-bromo acetanilide from acetanilide and meta-dinitrobezene from nitrobenzene.
Suggested Readings:
• ArunbBahl and B. S. Bahl:Advanced Organic Chemistry, S. Chand. (2019)
• L. Finar:Organic Chemistry (Vol. I & II), E. L. B. S. (2002)
• R. T. Morrison & R. N. Boyd:Organic Chemistry, Prentice Hall. (2011)

Session Plan

Session 1

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Session 2

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    Dr Sitaram Swain

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    Dr Sitaram Swain has received PhD degree from Utkal University in the year 2017. He is also trained and experienced from TATA Memorial Hospital, Mumbai, India. He has experienced with cell line culture, clinical biochemistry, immuno-fixation, immunoassay, cancer cytogenetic, serum protein electrophoresis and tumour marker analysis. He has qualified NET(ICAR-ASRB) in Animal biotechnology. He has […]