PRODUCTS OF ISOPRENE METABOLISM

Acetoacetyl-CoA + Acetyl-CoA

CH 2COO-
CH3C(OH)CH 2COSCoA
3-OH-3-methylglutaryl-CoA
Ergot Alkaloids
(fungi)
1.1.1.32

CH2COO-
CH 3C(OH)CH 2CH2OH
n
PHYTYL SIDE CHAINS Mevalonate Natural Rubber
CH3 Isoprene blue haze
HO 2.7.1.36
CH3 2.7.4.2 Isopentenyl adenosine
CH3 O
CH3 CH2COO-
a-Tocopherol (Vitamin E) CH 3C(OH)CH 2CH 2OP-O-P Plant Monoterpenes
CH2OH
O Diphospho mevalonate
CH3
4.1.1.33

O CH 2
Phylloquinone (Vitamin K) CH 3 Geraniol Limonene
CH 3C = CHCH 2OP-O-P CH3C.CH 2CHOP-O-P
5.3.3.2
Dimethylallyl- P-O-P Isopentenyl-P-O-P Perfumes Colour s
Chlorophyll side chain (C5) (C5)
2.5.1.1 OH
CHO
CH 2OP-O-P

Phytyl-P-O-P CH2 OP-O-P Menthol Citronellal Flavours

Geranyl- P-O-P
(C10) Dolichol Insect Hormones Zingiberene (ginger)
O CH2OP-O-P
2.5.1.10
CH3O CH3
Gibberellins - Plant growth hormones
CH3O n
O Ubiquinone Hopanoids
+
(Coenzyme Q) Farnesyl-P-O-P
2.5.1.29 (C15)

Menaquinone
2.
5.

(Vitamin K2)
1.
21

CH2OP-O-P
Plastoquinone
Geranyl-geranyl-PP
(C20) Squalene
2.5.1.32
(C30)

1.14.99.7
5.4.99.7
Phytoene
HO
CAROTENOIDS (C 40)
Lanosterol
(C30)
Colour
Lycopene HO
(C 40)
Colour Zymosterol

Light harvesting
pigments in i -CAROTENE
B
(C 40) HO
Photosynthesis
To brain - VISION Desmosterol
Xanthophylls
1.13.11.21 LIGHT
HO

Metarhodopsin Rhodopsin CHOLESTEROL

STEROIDS
COO- Opsin
Retinoate CHO
Ergosterol Pregnenolone Progesterone
5.2.1.3 (yeast)
trans-Retinal 11-cis-Retinal CHO
1.2.1.36 Light
Retinol esters 1.1.1.105 Aldosterone Testosterone
2.3.1.76 CH2OH Calciferol Finasteride
3.1.1.21
trans-Retinol
5.2.1.7
11-cis-Retinol CH2OH (Vitamin D)
Dark Cortisol Estradiol
(Vitamin A) Dihydro-
testosterone

These two minimaps are designed to stimulate the imagination and hopefully create excitement and an
awareness that we are dealing with REAL- LIFE METABOLISM. The facing one is entitled Isoprene
Metabolism and is a traditional biochemical pathways map but is itself interesting because it shows that
two very differing types of products- one mainly open-chain (carotenoid) and the other ringed (steroid )- can
arise from the same source. The facing map Isoprene Products is identical except that, in addition, it
highlights and pictures the real- -life significance of some of these products They include natural rubber;
plant and insect hormones and the side chains of many vitamins and of chlorophyll. They provide colour,
smell and flavour in many plant pr oducts such as carrots, lemons or roses. They include some of the vital
reactions that can convert light into vision and, in a different pathway, the steroids including estrogens and
testosterones with all their implications. Many of the sensual and sexual pleasures of life can thus be seen
to derive from the same, simple 5 -carbon compound isoprene. This is real-life metabolism.

Designed by Donald Nicholson c 2002 IUBMB