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PORPHYRINES O S Chlorophyll

Porphyrins p y
Porphyrins (pronounce) are tetrapyrroles. They consist of four weakly aromatic pyrrole (pronounce) rings joined by methene bridges. Porphyrin is a heterocyclic macrocycle made from 4 pyrrole subunits linked li k d on opposite sides ( position) through 4 methinebridges ( CH ) it id ( iti ) th h thi b id (=CH-). The extensive conjugated system makes the compound chromatic, hence the name porphyrin from a Greek word for purple porphyrin, The macrocycle has 22 pi electrons, 18 of which are active in the conjugated system. j g y These are the central groups of biologically imp molecules such as Hemoglobin, Myoglobin, Chlorophyll, Cytochromes, etc

Uses of Porphyrins
Because of the unique chemistry of porphyrins, they are able to perform Several functions: As a metal binder (ligands) As A a solar cell (convert light or chemical energy) l ll ( t li ht h i l ) As an oxygen transport medium (hemoglobin) As an electron transfer medium (conducting polymers) Gene regulation Drug metabolism Iron metabolism Hormone synthesis

As the basic building block of hemoglobin


Heme a cross-coupled p p y porphyrin used in the larger g molecule hemoglobin

Cytochrome C a molecule responsible for transporting an electron used to provide energy to the organism. These molecules are identical, or very similar, for related species of plants or animals.

Chlorophyll
A green compound found in leaves and green stems of plants. It occurs in cell organelles called chloroplasts, which are absent in animals. Chlorophyll is the molecule that traps this 'most elusive of all powers and is called a photoreceptor. The basic structure of a chlorophyll molecule is a porphyrin ring, coordinated to a central atom. di t d t t l t This is very similar in structure to the heme group found in hemoglobin, hemoglobin except that in heme the central atom is iron, whereas in iron chlorophyll it is magnesium.

Chlorophyll a and chlrophyll b


The most important pigment in plants is chlorophyll. Two types of chlorophyll in plants, chlorophyll a (chl a) and plants chlorophyll b (chl b) Chlorophyll is composed of two p ; the first is a porphyrin ring p y p parts; p p y g with magnesium at its center, the second is a hydrophobic phytol tail The ring has many delocalized electrons that are shared between several of the C, N, and H atoms; these delocalized electrons are very important for the function of chlorophyll. The tail is a 20 carbon chain that is highly hydrophic and stabilizes the molecule in the hydrophobic core of the thylakoid membrane.

Structurally CH3 group is present in chl a where chl b has a CHO group. Chlorophyll a and b absorb different wavelengths better than others. chl a absorbs best at 450 and 680 nm chl b absorbs best at 500 and 640 nm chlorophyll a is directly involved in the redox reactions of the light reactions, chl b functions as an accessory pigment Accessory pigments absorb light and pass the energy from the light t th hl in th li ht to the chl a i the reaction center ti t Other accessory pigments can be present such as xanthophylls and the more well known carotenoids carotenoids. The most well known carotenoid is beta-carotene which absorbs d e e t wave e gt s t a t e c o op y s. different wavelengths than the chlorophylls.

Photosystems
Within the thylakoid membranes of the chloroplast, are two photosystems. Photosystem I optimally absorbs p y p y photons of a wavelength of 700 nm. g Photosystem II optimally absorbs photons of a wavelength of 680 nm. Photosystem II uses light energy to oxidize two molecules of water into one molecule of molecular oxygen. The 4 electrons removed from the water molecules are transferred by an electron transport chain to ultimately reduce 2NADP+ to 2NADPH. During the electron transport process a proton gradient is generated across the thylakoid membrane. This proton motive force is then used to drive the synthesis of ATP. This Thi process requires PSI PSII cytochrome bf f i PSI, PSII, h bf, ferredoxin-NADP+ d i NADP reductase and chloroplast ATP synthase.

Photosystem I
Contains the chlorophyll-a molecule P700 p y Absorbs light maximally at 700 nm Receives energy from photons, from associated accessory pigments in its antenna system, and from the electron transport chain from Photosystem II. Uses the energy from light to reduce gy g NADP+ to NADPH + H+, or simply to power a proton pump (plastoquinone, or PQ).

Photosystem II
Contains the chlorophyll-a molecule P680 p y Absorbs light maximally at 680 nm Receives energy from photons and from associated accessory pigments in its antenna system.

Uses the energy from light to oxidise water gy g molecules, producing protons (H+) and O2 as well as passing an electron to the electron transport chain.

Both h t B th photosystems are required for t i df noncyclic electron transport

Only Photosystem I participates in cyclic O l Ph t t ti i t i li electron transport,

Chlorophyll A and B g y absorb light mostly in the red and blue regions of the p spectrum Carotene and xanthophyll absorb li h from other b b light f h regions and pass the energy to chlorophyll