Isoprenoides by KK Sahu sir

CONTENTS
INTRODUCTION
DEFFINATION
TERPENE- GENERAL INFORMATION
CHEMICAL COMPOUND
ISOPENOID OF PLANT AND ANIMAL
NATURAL CCURANCE
INDUSTRIAL PRODUCTS
NATUR OF ISOPRINOIDS
NATURAL PRODUCTS
SECONDARY METABOLITES
BRANCHED CHAIN ALCOHOL
STRUCTURAL CLASSIFICATION OF ISOPRENOIDS
HAID TO TAIL
TAIL TO TAIL
TYPES OF ISOPRENOIDES
ISOLATION AND IDENTIFICATIN OF ISOPRENOIDES
PURIFICATION
DETERMINATION
BIOSYNTHESIS OF ISOPRINOIDS
MEVOLANATED PATHWAY
NAN- MEVOLANATED PATHWAY
USES OF ISOPRENOIDES
OTHER APPLICATION
ISOPRINOID SYNTHESIS IN DNA REPLICATION AND CELL GROTH
OTHER MEMBRANE ASSOSIATED ISOPRINOIDS
CONCLUSION
REFRANCES

1. ISOPRENOIDES
By
KAUSHAL KUMAR SAHU
Assistant Professor (Ad Hoc)
Department of Biotechnology
Govt. Digvijay Autonomous P. G. College
Raj-Nandgaon ( C. G. )

2. CONTENTS
INTRODUCTION
DEFFINATION
TERPENE-GENERAL INFORMATION
CHEMICAL COMPOUND
ISOPENOID OF PLANT AND ANIMAL
•NATURAL CCURANCE
•INDUSTRIAL PRODUCTS
NATUR OF ISOPRINOIDS
•NATURAL PRODUCTS
•SECONDARY METABOLITES
•BRANCHED CHAIN ALCOHOL
STRUCTURAL CLASSIFICATION OF ISOPRENOIDS
•HAID TO TAIL
•TAIL TO TAIL
TYPES OF ISOPRENOIDES
ISOLATION AND IDENTIFICATIN OF ISOPRENOIDES
•PURIFICATION
•DETERMINATION
BIOSYNTHESIS OF ISOPRINOIDS
•MEVOLANATED PATHWAY
•NAN-MEVOLANATED PATHWAY
USES OF ISOPRENOIDES
OTHER APPLICATION
•ISOPRINOID SYNTHESIS IN DNA REPLICATION AND CELL GROTH
•OTHER MEMBRANE ASSOSIATED ISOPRINOIDS
CONCLUSION
REFRANCES

3. (1) INTRODUCTION
•Isoprene(shortforisoterpene),or2-methyl-1,3-butadiene,isa
common organiccompound withtheformulaCH2=C(CH3)CH=CH2.
•Understandardconditionsitisacolorlessliquid.However,this
compound ishighlyvolatilebecauseofitslowboilingpoint.
•Thefunctionalisopreneunitsinbiologicalsystemsaredimethylallyl
diphosphate(DMADP) anditsisomerisopentenyldiphosphate(IDP).
•Theselipidsareconsideredtobethelargestgroupofnatural
products,playingawidevarietyofrolesinphysiologicalprocessesof
plantsandanimals,andhavinganumberofcommercialuses.
(2)DEFFINATION
“Anyofaclassoforganiccompounds (organiccompound)
composedoftwoormoreunitsofhydrocarbons(hydrocarbon),with
eachunitconsistingoffivecarbonatomsarrangedinaspecific
pattern.”

4. (4)TERPENE –GENERAL INFORMATION
•Geraniol(acontributortoroseperfumes;fromgeranium
oil)
•menthol(frompeppermintoil),
•citral(fromlemongrassoil),
•imonene(fromlemonandorangeoils),
•pinene(fromturpentine),andcamphoreachhavetwo
isopreneunits.
•moreunitsincludephytol,aprecursorofchlorophyll;
•squalene,theprecursorofcholesterolandothersteroids;
•lycopene,theredpigmentintomatoesand
•animportantphytochemical;andcarotene,thepigment
incarrotsandaprecursorofvitaminA.

5. (5)Chemicalcompound
•Isoprenoidsinlivingorganismsrangeinfunction
frompigments (pigment)andfragrances to
vitamins (vitamin)andprecursors ofsex
hormones(sexhormone).
•Othercommercially valuableisoprenoidsare
thoseusedasflavourings,solvents,andraw
materialsforchemicals.
•Thenameterpenespecificallyreferstonaturally
occurringcompounds thatarederivativesofa
singleisopreneunit,Thewordterpenecomes
fromanolderspellingofturpentine(terpentine),
acleanerthatisamixtureofisoprenoids
(originallytheresinoftheterebinthplant).

6. (6)Iprenoidsofplantsandanimals
Intheessentialoilswhicharefoundinthegummyexudatesofmany
treesandshrubs.
Plantisoprenoidseffectgrowth(e.g.,gibberellicacid(carotenoids).
Inanimals,fishliveroils,woolwax,andtheyellowpigmentsinegg
yolk,butterfat,feathers,andfishscales.
Thelaticesofafewspeciesofplantscontainthepolyterpene
hydrocarbonsrubberorgutta-percha.
Thepresenceofmenthol,citral,camphor,limonene,orα-pinene.
plantsubstancespreventthematurationoftheinsect,
TetraterpenecarotenoidpigmentsarethesourceofvitaminA.
isoprenoidincludevitaminE,importantinreproduction,andvitamin
K,necessaryfortheblood-clottingprocess.
Theubiquinones(ubiquinone)(coenzymeQ).
Ininsects(insect),certainisoprenoidsubstancesinfluencematuration
andmatingbehaviour,
Theso-calledprenylatedproteinsdonotfunctionwithoutthe
isoprenoid.
Steroids(steroid),aclassofcompoundsofgreatimportanceinboth
plantsandanimals.

7. (7)OCCURRENCE
(A)Naturaloccurrence
Isopreneisproducedandemittedbymanyspeciesoftreesintotheatmosphere
(majorproducersareoaks,poplars,eucalyptus,andsomelegumes).
•Isopreneproductionfromplants
Isopreneemissionincreasesdramaticallywithtemperatureandmaximizesat
around40°C.(thermotolerancehypothesis).
•Regulationofisopreneemission
Isopreneemissioninplantsiscontrolledbothbytheavailabilityofsubstrate
(DMADP)andbyenzyme(isoprenesynthase)activity
•Biologicalroles
•sunnydays,upto25μg/(gdry-leaf-weight)/hourinmanyoakspecies.
•Isopreneinotherorganisms
Theestimatedproductionrateofisopreneinthehumanbodyis0.15µmol/(kg•h),
equivalenttoapproximately17mg/dayforapersonweighing70kg.

8. (B)Industrial production
About 800,000 tonnesare produced annually. About 95% of isoprene production is used to
produce cis-1,4-polyisoprene—a synthetic version of natural rubber.
•Aims
1. Engineer yeast and E. coli cells for efficient production of isoprenoidcompounds
(isoprenoidpathway engineering
2. Develop efficient isoprene production strains
3. Develop strains which produce isoprenoidswith aviation fuel properties.
•They are all produced from common five-carbon building blocks, isopentenyl
pyrophosphate (IPP) and dimethylallylphyrophosphate(DMAPP).
We are interested in two types of isoprenoids:
(1)Isoprene, a chemical feedstock which is polymerized to make rubbers and
elastomers.
(2)Higher-order isoprenoidcompounds with aviation fuel properties
.

10. ApplicationExample Details/ApplicationsIsoprenoidGroup
Pharmaceu
tical
Taxol
Limonene
Artemisinin
Chemotherapeutic
Anti-cancer agent
Anti-malarial agent
Diterpene derivitive
Monoterpene
Sesquiterpene
Food
Additive/
Supplemen
t
Carotenoids
Menthol
Tocopherol
Coenzyme Q10
Colourants
Flavour
Antioxidant
Antioxidant
Tetraterpenes
Monoterpene
Diterpenederivative
Sesquiterpenederivitive
Agriculture
/
Floriculture
Abscisic acid
Eucalyptol,
limonene
Gibberellin
Plant propagation
Insecticidal
Increases life of cut
flowers
Tetraterpene
Monoterpenes
Diterpene
Isoprenoid compounds (downstream products) with industrial applications

11. Industrial
chemical
Isoprene
Various
monoterpenes
Feedstock for synthetic
rubbers
Fragrances
Hemiterpene
Monoterpenes
Fuels/ fuel
replacements
Squalene
Isopentenol
Fernesene,
farnesol
Bio-crude
Gasoline replacement
Jet fuel
Sesquiterpene
derivitive
Hemiterpene
alcohol
Sesquiterpene
Fuel additives
Isoprenoid
alkenes, alkanes,
alcohols
Increase octane ratings,
anti-corrosives, lubricants
Several different
classes

12. (8) NATURE OF ISOPRENOIDS
(A)NATURAL PRODUCTS :
Natural products are secondary metabolites of an organism.
“natural products” can be sub-divided in to terpenoids, alkaloids, shikimates, and
polyketides
(B) SECONDARY METABOLITES
Terpenoids (come from semiterpene oligomerization)
Azadirachtin, (Neem tree)
Artemisinin, present in Artemisia annua Chinese wormwood
tetrahydrocannabinol, present in Cannabis
Steroids (Terpenes with a particular ring structure)
Saponins (plant steroids, often glycosylated)
(C) BRANCHED CHAIN ALCOHAL
-Polyisoprenoid alcohols
A -Saturated polyisoprenoids (Isopranols)

13. B -Unsaturated polyisoprenoids (prenols or polyprenols)
Polyprenols are present in several bacteria, where they act as lipid carriers in the
biosynthesis of cell surface polymers.
-1. all trans forms :
Geraniol(fromroseoil)alsoaneffectivemosquitorepellent.itisproducedbythescent
glandsofhoneybees.
Farnesolisprenol.Itispresentinmanyessentialoilssuchascitronella,neroli,
cyclamen,lemongrass,rose,andothers.
Geranylgeraniolistheacylationofproteinsandthesynthesisofvitamins(VitaminsE
andK)..
Phytolisapartiallysaturatedditerpene:
n
Number of isoprene unit Number of carbons Name
0
2 10 Geraniol
1
3 15 Farnesol
2
4 20 Geranylgeraniol
3
5 25 Geranylfarnesol
7
9 45 Solanesol
8
10 50 Spadicol

14. 2. ditrans-polycis-prenols,
Bacteriaprenol type
•3. tritrans-polycis-prenols,
Ficaprenoltype
4. dolichol types,

15. (9) STRUCTURAL CLASSIFICATION OF ISOPRINOID S
Haid to tail coupling
Tail-to-tail coupling

16. Sesquiterpenes
(10) TYPES OF ISOPRINOIDS
Monoterpenes
It has been found in other fish liver oils, in vegetable oils, in fungi (fungus), and in human
earwax and sebaceous secretions.
They are volatile oils, less dense than water, and have normal boiling points (boiling
point) in the range of 150 to 185 °C (300 to 365 °F)

17. Diterpenes
phytol, an oxygenated acyclic diterpene, is an important building block of the chlorophyll
molecule.
Triterpenes
The biochemical importance of squalene as a metabolic intermediate in the biosynthesis of
cholesterol .
Tetraterpenes
The yellow, orange, or red fat-soluble plant and animal pigments, known as carotenoids
(carotenoid), are classed as tetraterpenes.
Polyterpenes
rubber, which occurs in the latex of the rubber tree, is a polyterpene hydrocarbon, in which n is
4,000–5,000.

18. (11) ISOLATION AND IDENTIFICATIN OF ISOPRENOIDES
•PURIFICATION
•DETERMINATION
(12)BIOSYNTHESISOFISOPRINOIDES
Isopentenyldiphosphate(IPP),theuniversalbuildingblockforallisoprenoidsis
formedbytwodifferentbiosyntheticroutes:thewellknownacetate/mevalonate
pathwayandthenonmevalonatepathwaystartingfrompyruvateand
grycereldihyde3-phosphate.
Incontrasttotheclassicalmevalonatepathwayofisoprenoidbiosynthesis,
plantsandapicomplexanprotozoasuchasmalariaparasiteshavetheabilityto
producetheirisoprenoids(terpenoids)usinganalternativepathway,thenon-
mevalonatepathway,whichtakesplaceintheirplastids.Inaddition,mostbacteria
includingimportantpathogenssuchasMycobacteriumtuberculosissynthesizeIPP
andDMAPPviathenon-mevalonatepathway.

21. Reactants Enzyme Product
Pyruvate and
glyceraldehyde 3-
phosphate
DOXP synthase(Dxs)
1-Deoxy-D-xylulose 5-phosphate
(DOXP)
DOXP DOXP reductase(Dxr, IspC)
2-C-methylerythritol 4-
phosphate (MEP)
MEP
4-diphosphocytidyl-2-C-
methyl-D-erythritol synthase
(YgbP, IspD)
4-diphosphocytidyl-2-C-
methylerythritol (CDP-ME)
CDP-ME
4-diphosphocytidyl-2-C-
methyl-D-erythritol kinase
(YchB, IspE)
4-diphosphocytidyl-2-C-methyl-
D-erythritol 2-phosphate (CDP-
MEP)
CDP-MEP
2-C-methyl-D-erythritol 2,4-
cyclodiphosphate synthase
(YgbB, IspF)
2-C-methyl-D-erythritol 2,4-
cyclopyrophosphate (MEcPP)
MEcPP
HMB-PP synthase (GcpE,
IspG)
(E)-4-Hydroxy-3-methyl-but-2-
enyl pyrophosphate (HMB-PP)
HMB-PP HMB-PP reductase (LytB, IspH) IPP and DMAPP

22. Inhibition
Fosmidomycin specificallyinhibitsDOXPreductoisomerase, akey
enzymeinthenon-mevalonatepathway,andthereforerepresentsan
attractivecandidateasantibioticorantimalarialdrug.
Tcellactivation
TheintermediateHMB-PPisthenaturalactivatorforhumanVγ9/Vδ2T
cells,themajorγδTcellpopulationinperipheralblood.
(13)Usesofisoprenoids
(15)OTHERSIMPORTANCE
•RoleofisoprenoidsynthesisinDNAreplicationandcellgrowth

23. (b) OTHER MEMBRANE -ASSOCIATED ISOPRENOIDS
STRUCTURES, BIOCHEMISTRY AND FUNCTION
1.
1. Plastoquinone
2. Ubiquinone (Coenzyme Q)
3. Phylloquinone (Vitamin K)
Phylloquinone or 2-methyl-3-phytyl-1,4-naphthoquinone is synthesised in the chloroplasts of plants
where it is a key component of the photosystem I complex and serves as an electron acceptor.

24. 5.Retinol(VitaminA)
Theterm‘vitaminA’isusedtodenoteretinolorall-trans-retinoland
afamilyofbiologicallyactiveretinoidsderivedfromthis.Theseare
onlyfoundinanimaltissues,thebiosyntheticprecursorsofthese
compounds areplantcarotenoids(provitaminA).
6.Undecaprenyl Phosphate and Lipid II
Undecaprenyl phosphate (a C
55
isoprenoid), also referred to as
bactoprenol, is a lipid intermediate that is essential for the
biosynthesis of peptidoglycan and many other cell -wall
polysaccharides, and for N-linked protein glycosylation in prokaryotes
(both in Gram-negative and Gram-positive bacteria).

25. 7.Farnesy Pyrophosphate and Related Compounds
Farnesyl pyrophosphate is a key intermediate in the biosynthesis of
sterols such as cholesterol and it is the donor of the farnesyl group for
isoprenylation of many proteins (see the web page on proteolipids).

26. (1 ) Lehninger Principle of biochemistry:
David L.NelsonMichael M.Cox
(2) TODD & HOWARDS MASON –
BIOCHEMISTRY ,4
th
EDITION
Websites:
www.kbiotech.com
www.wikipedia.com