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    Xenobiotic Degradation

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    eyob
    This document discusses the biodegradation of xenobiotic compounds by microorganisms. It defines xenobiotics as artificially synthesized compounds used for industrial or agricultural purposes, such as pesticides and polychlorinated biphenyls. It then outlines various sources of xenobiotic compounds from industries like petrochemical, plastic, and pesticide production. The document also discusses mechanisms by which microbes can degrade recalcitrant compounds like halogenated hydrocarbons through processes like reductive dehalogenation and oxidative dehalogenation. Specific examples covered include the degradation of polyaromatic hydrocarbons, polychlorinated biphenyls, DDT, and atrazine.

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    Xenobiotic Degradation

    Uploaded by

    eyob
    66 views22 pages
    This document discusses the biodegradation of xenobiotic compounds by microorganisms. It defines xenobiotics as artificially synthesized compounds used for industrial or agricultural purposes, such as pesticides and polychlorinated biphenyls. It then outlines various sources of xenobiotic compounds from industries like petrochemical, plastic, and pesticide production. The document also discusses mechanisms by which microbes can degrade recalcitrant compounds like halogenated hydrocarbons through processes like reductive dehalogenation and oxidative dehalogenation. Specific examples covered include the degradation of polyaromatic hydrocarbons, polychlorinated biphenyls, DDT, and atrazine.

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    XENOBIOTIC DEGRADATION

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    This document discusses the biodegradation of xenobiotic compounds by microorganisms. It defines xenobiotics as artificially synthesized compounds used for industrial or agricultural purposes, such as pesticides and polychlorinated biphenyls. It then outlines various sources of xenobiotic compounds from industries like petrochemical, plastic, and pesticide production. The document also discusses mechanisms by which microbes can degrade recalcitrant compounds like halogenated hydrocarbons through processes like reductive dehalogenation and oxidative dehalogenation. Specific examples covered include the degradation of polyaromatic hydrocarbons, polychlorinated biphenyls, DDT, and atrazine.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    66 views22 pages

    Xenobiotic Degradation

    Uploaded by

    eyob
    This document discusses the biodegradation of xenobiotic compounds by microorganisms. It defines xenobiotics as artificially synthesized compounds used for industrial or agricultural purposes, such as pesticides and polychlorinated biphenyls. It then outlines various sources of xenobiotic compounds from industries like petrochemical, plastic, and pesticide production. The document also discusses mechanisms by which microbes can degrade recalcitrant compounds like halogenated hydrocarbons through processes like reductive dehalogenation and oxidative dehalogenation. Specific examples covered include the degradation of polyaromatic hydrocarbons, polychlorinated biphenyls, DDT, and atrazine.

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    Biodegradation of

    Xenobiotic
    compounds

    Dr. A. Suresh Ph.D


    Assistant Professor
    College of Biological and Chemical Engineering 1
    Department of Biotechnology
    Phone:0902643433, blueyellowsnu@gmail.com
    • Xenobiotics : compound have been
    produced artificially by chemical
    synthesis for industrial or agricultural
    purposes e.g. halogenated HC.,
    aromatics, pesticides, PCB
    (polychlorinated biphenyls ), PAH
    ( polyaromatic hydrocarbons ).
    • Recalcitrant : compound totally resistant
    to biodegradation
    2
    Source of xenobiotic compounds
    1. Petrochemical industry : oil/gas industry, refineries, and the production
    of basic chemicals e.g. vinyl chloride and benzene
    2. Plastic industry :
    - uses a number of complex organic compounds
    such as anti-oxidants, plasticizers, cross-linking agents
    3. Pesticide industry : Benzene and benzene derivatives, often chlorinated
    and often heterocyclic
    4. Paint industry : major ingredient are solvents,
    xylene, toluene, methyl ethyl ketone, methyl
    isobutyl ketone and preservatives
    5. Others : Electronic industry, Textile industry, Pulp
    and Paper industry, Cosmetics and Pharmaceutical
    industry, Wood preservation

    3
    Why compounds are recalcitrant?
    1. Failure of the compound to induce the synthesis of
    degrading enzyme.
    2. Failure of the compound to enter the m.o. cell for lack of
    suitable permease.
    3. Unavailability of the compound due to insolubility or
    adsorption.
    4. Excessive toxicity of the parent compound
    or its metabolic products.
    5. Unavailability of the proper electron acceptor.
    6. Unfavorable environmental factors e.g. temp.,
    4
    light, pH, O2 , moisture.
    Bacteria and algae
    Ring cleavage

    Acetly CoA Acetaldehyde and pyruvic acid

    Kreb cycle Kreb cycle

    Aerobic degradation
    of aromatic compounds
    (PAHs)
    5
    Halogenated Xenobiotic (herbicide &pesticide)

    Microbes by monooxygenase and dioxygenase

    6
    Mechanisms of Dehalogenation

    1) Reductive dehalogenation : two-electron transfer


    reaction which involves the release of the halogen as a
    halogenide ion and its replacement by hydrogen
    Cl Cl H Cl
    - -
    C C + XH C C + Cl + X
    Cl Cl Cl Cl

    2) Oxidative dehalogenation : catalyzed by mono- or


    dioxygenases, which incorporate atom of molecular
    oxygen into the substrate
    COOH OH
    Cl OH

    + O2 + NADPH + H+ + NAD+ + CO2 + HCl


    7
    3) Hydrolytic dehalogenation : catalyzed by halido-
    hydrolases, the halogen is replaced by a OH group
    which is derived from water.

    COOH Cl COOH OH

    -
    H2O Cl

    8
    5) Dehydrodehalogenation : HX is eliminated from the
    molecule, leading to the formation of a double bond
    Cl
    Cl Cl Cl
    Cl
    + HCl

    Cl Cl Cl Cl
    Cl Cl

    7) Hydratation : a hydratase-catalyzed addition of water


    molecule to an unsaturated bond can yield dehalogenation
    of vinylic compounds
    HOOC-CH=CHCl + H2O [ HOOC-CH2-CHOHCl]

    HOOC-CH2-CHO + HCl 9
    • Most fungi oxidize PAHs via a cytochrome P450
    catalyzed mono- oxygenase reaction to form
    reactive arene oxides that can isomerize to
    phenols

    10
    11
    PCBs
     Synthesized chemicals from petro-chemical
    industry used as lubricants and insulators in
    heavy industry
     Used because
     Low reactivity
     Non-flammable
     High electrical resistance
     Stable when exposed to heat and pressure
     Hydraulic fluid  Plasticizers
     Casting wax Uses  Pigments
     Carbonless carbon  Adhesives
    paper  Liquid cooled electric
     Compressors motors
     Heat transfer systems  Fluorescent light
    ballasts
    Where found
     They are ubiquitous:
     Water: rain and groundwater
     Soil: through direct disposal and leaching from disposal
    sites
     Animals: bioaccumulation
     Food: bioaccumulation and production methods
    Risks
     PCBs are toxic
     Soluble in fats, oils, solvents
     Some more than others: more Cl = more toxic
     carcinogenous:  reproductive system
     Liver cancer  humans and animals
     melanoma  reduced birth weight
     immune system  reduced conception weight
     studies done on rhesus
    monkeys which have similar  decrease in gestational ages
    systems  still births and abortions
     effects noted in people
    exposed to PCB
    contaminated rice oil
     suppressed
     swollen thymus gland in
    infants
    Human Health
     carcinogenous:  reproductive system
     Liver cancer
     melanoma
     humans and animals
     immune system  reduced birth weight
     studies done on rhesus  reduced conception
    monkeys which have similar weight
    systems
     effects noted in people  decrease in gestational
    exposed to PCB ages
    contaminated rice oil
     still births and abortions
     suppressed
     swollen thymus gland in
    infants
    Bioremediation
     The process by which organisms use toxic
    chemicals as a food source in an environment
    which is favorable to that process

     Generally enhanced by addition of nutrients,


    oxygen, moisture or adjusting pH levels
    Pathways of PCB Degradation
     Anaerobic/Aerobic removal
     Photochemical Degradation
     Thermal Degradation
     Fungal Degradation
    Methods for PCB removal
     Natural Attenuation:
     Biostimulation:
     Bioaugmentation:
     Microbes either:
     Use PCBs as a carbon source
     Microbes initiate reductive de-chlorination
     Problems
     Generally slow
     Use other carbon sources in natural systems first
     Microbes prefer lower chlorinated biphenyl
    Pathways of Aerobic Degradation

    Acinetobacter

    18
    •DDT (dichloro-diphenyl-trichloroethane) is the first
    of a number of chlorinated H.C. to be developed as
    pesticides in 1939

    • Pesticides can be classified in a number of different


    ways for example; by their chemical nature ( natural
    organic cpd., inorganic cpd., chlorinated
    hydrocarbon, organophosphates, carbamates)

    19
    20

    Proposed pathways for the microbial degradation of DDT


    21
    Atrazine: herbicide, recalcitrant

    Recently, bacterial degradation (mixed)

    Clavibacter

    Pseudomonas

    22

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