Bioorganic chemistry - Week 4

What are the major roles of carbohydrates?

Structure (celluloes), energy and metabolism and signalling and cellular communication

In chair confirmation what is the ‘Up and down’ direction called

Axial

In chair confirmation what is the ‘across’ direction called

Equatorial direction

What position do large functional groups prefer?

the equatorial position, as axial positions experience more steric strain than equitorial because the equitorial position has more space.

Does a beta glucose has what positioning?

Equatorial

Does alpha glucose have what positioning?

Axial positioning

What is the anomeric effect?

The anomeric effect occurs in axial positioning of the C-1 anomeric carbon. The axial positioning allows for more overlap of n and sigma* orbtials, meaning higher amount of electrons delocalised and therefore higher molecule stability (similar to beta-glucose even though the equatorial position is typically a lot more stable than the axial position due to steric hinderance)

Is cellulose B-glucose or alpha-glucose? How do we know this?

Cellulose is B-glucose as it is a very rigid structure that can only be created with equatorial positioning.

What are primary metabolites?

They are essential for life (BIG 4 - nucleic acids, carbohydrates, DNA and lipids)

What are secondary metabolites?

compounds synthesises by living systems that aren’t essential to life but could provide longer term benefit e.g. pheromones to attract a mate. Most of these are synthesised from primary metabolites.

Why do fatty acids have an even number of carbons?

Because Acetyl CoA adds 2 carbons per cycle in fatty acid biosynthesis.

What is a terpene?

It is a volatile, built from repeating isoprene units (5 carbon units)

allylic rearrangment

chemical process where a carbon-carbon double bond and a fucntional group migrate to an adjacent carbon atom within an isoprenoid structure

allylic shift

the double bond moves to the neighbouring carbon, frequently forming a new isomer

What are terpenoids?

Terpenoids are versatile organic compounds utilized across the fragrance, food, medicine, and agriculture industries for their distinct aromas, flavors, and biological properties.