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Stereochemistry of Natural Products

This document discusses the stereochemistry of natural products. It begins by defining stereochemical isomers as molecules with the same chemical formula and bond connectivity but different arrangements in three-dimensional space. It then defines natural products as chemical compounds produced by living organisms and found in nature, and notes they can also be synthesized artificially. Natural products are classified into categories like terpenoids, alkaloids, and steroids. The document goes on to discuss specific concepts in stereochemistry like chirality, optical activity, enantiomers, diastereomers, racemic mixtures, and Fischer projections.

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684 views14 pages

Stereochemistry of Natural Products

This document discusses the stereochemistry of natural products. It begins by defining stereochemical isomers as molecules with the same chemical formula and bond connectivity but different arrangements in three-dimensional space. It then defines natural products as chemical compounds produced by living organisms and found in nature, and notes they can also be synthesized artificially. Natural products are classified into categories like terpenoids, alkaloids, and steroids. The document goes on to discuss specific concepts in stereochemistry like chirality, optical activity, enantiomers, diastereomers, racemic mixtures, and Fischer projections.

Uploaded by

Aria Domingo
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Stereochemistry of

Natural Products

By: Maryam Al-Saeed


Duaa Alotaibi
Supervised by:
Dr. Samar Aabubshait
Stereochemical isomers:

Stereochemical isomers are molecules, which have the same


chemical formula and bond connectivity but different relative
arrangement in three dimensional space.it is also known as
3D chemistry.
Natural Products
-Natural product is a chemical compound or substance
produced by a living organism, that is found in nature.
In the broadest sense, natural products include any
substance produced by life.

-Natural products can also be prepared by chemical


synthesis and have played a central role in the
development of the field of organic chemistry by
providing challenging synthetic targets.

-The term natural product has also been extended for


commercial purposes to refer to cosmetics, dietary
supplements, and foods produced from natural sources
without added artificial ingredients.
Natural products are classified into several categories , one of them is:

Natural Product
(secondary metabolites)

Phenolic
Terpenoids Alkaloids Steroids
compounds

Menthol Caffeine Cholesterol Phenols


Chirality
They are non-superimposable mirror images of
each other. Achiral objects, on the other hand,
are easily superimposable on each other.

Each chiral carbon must have four different groups. For


example, cholesterol have eight chiral centres

Cholesterol
Optical Activity

- Each enantiomer of a chiral structure reacts


differently with polarized light.

- Polarized light is light were only one plane of


polarization is chosen by a polarization filter.

- When this light is travelling through a chiral


substance, the plane of rotation will change.

- Here in this example,(-).carvone has an angle


of rotation of -72°,(+).carvone one of +72 °.
(limonene) the compound which gives different taste to lemon and
orange are examples of stereochemical isomers.
Enantiomer
If a molecule is non-superimposable on its mirror
image, then the molecule is said to have enantiomeric
relationship with its mirror image molecule.
Terpene
Linalool has two enantiomeric forms
which are both found in nature.
(R)-(-)-linalool enantiomer is responsible
for the fragrant scent in lavender and
sweet basil.
The (S)-(+)-linalool enantiomer is largely
found in essential oils of coriander seed
and sweet orange flowers. 
(In 1884, By Louis Pasteur) found two of the four possible stereoisomers
(R,R)- and (S,S)- are enantiomers but the 3rd and 4th isomers called a meso
compound due to (plane of symmetry)
- Meso is (optically inactive) diastereomers of chiral stereoisomers.
The meso form of tartaric acid is a diastereomer of the other forms.

Diastereomer:
Diastereomerism occurs if both molecules contain two or more chiral
centers, but if only one of the chiral centers in each molecule is
different than the other, then the two molecules are diastereoisomer.
Racemic mixtures:
Racemate is one that has equal amounts of left- and right-handed
enantiomers of a chiral molecule. an equimolar mixture will not
give any optical rotation at all.

The first known racemic mixture was


racemic acid, which Louis Pasteur found
to be a mixture of the two enantiomeric
isomers of tartaric acid:
Fischer
Projection:
Fischer projection created by the German chemist
Emil Fischer in 1891, is a convention used to depict a
stereoformula
in 2D without destroying the stereochemical
information.

It is a representation of a 3D molecule as a flat structure where a


tetrahedral carbon is represented as two crossed lines. ). For
example, Asparagine, The two vertical bonds is (towards the
viewer) while the horizontal bonds is away from the viewer.
Stereochemistry of
References: Natural Products
• Introduction to Natural Products and Medicinal Chemistry, David LEMIN. Chiba University 2005
• Chemistry of Plant Natural Products, Sunil Kumar Talapatra · Bani Talapatra
• Consumer Chemistry, A Brief History of Natural Products and Organic Chemistry Chapter 6
• Webster's Revised Unabridged Dictionary (1913). "Natural product". Free Online Dictionary and C. & G. Merriam Co. A chemical substance produced by a living
organism; - a term used commonly in reference to chemical substances found in nature that have distinctive pharmacological effects. Such a substance is considered a
natural product even if it can be prepared by total synthesis.
• "All natural". Nature Chemical Biology. 3 (7): 351. July 2007. doi:10.1038/nchembio0707-351. PMID 17576412. The simplest definition for a natural product is a
small molecule that is produced by a biological source.
• Samuelson G (1999). Drugs of Natural Origin: A Textbook of Pharmacognosy. Taylor & Francis Ltd,. ISBN 9789186274818.
• National Center for Complementary and Integrative Health (2013-07-13). "Natural Products Research—Information for Researchers | NCCIH". U.S. Department of
Health & Human Services. Natural products include a large and diverse group of substances from a variety of sources. They are produced by marine organisms,
bacteria, fungi, and plants. The term encompasses complex extracts from these producers, but also the isolated compounds derived from those extracts. It also includes
vitamins, minerals and probiotics.
• "About Us". Natural Products Foundation. Retrieved 2013-12-07. Natural products are represented by a wide array of consumer goods that continue to grow in
popularity each year. These products include natural and organic foods, dietary supplements, pet foods, health and beauty products, "green" cleaning supplies and more.
Generally, natural products are considered those formulated without artificial ingredients and that are minimally processed.
Stereochemistry of

Natural Products

Thank You.
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