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Organic Chem: Biochemistry

Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers smaller, simpler

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Page 1: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Organic Chem: Biochemistry

Page 2: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Biochemistry• Study of chem of living organisms

• Most: large, complex molecules

• complex molecules: biopolymers smaller, simpler

units: monomers

4 main classes:

1. lipids

2. Proteins

3. Carbohydrates

4. nucleic acids2

Page 6: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Carbohydrates: it’s all in the name!

-ose: fructose, glucose, maltose, lactose, galactose, sucrose, etc.

Page 7: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

An aldehyde sugar = aldose 6 C sugar = hexose

What other functional groups

do you see?

Page 8: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

A ketone sugar = ketose 6 C sugar = hexose

Structural isomer

Page 9: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Which atoms could be chiral?

Reminder: 4 diff groups

on a central C

Page 10: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Aldehyde double bond breaks and O atom transfers over H.

O then can form 2 single bonds to hold the ring

Intramolecular Reaction of Glucose to Form a Ring

Page 11: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 13: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Hydrolysis:

Page 14: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 15: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Proteins: the main molecule of living tissue

Page 16: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 17: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 18: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 19: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

All 20 aa’s are chiral except for Glycine.

 Amino acids

link together in condensation reactions to

form polymers.

Page 20: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Zwitterion

Page 21: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Condensation rxtn Forms C to N peptide bond

Page 22: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 23: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

201 = 20 amino acids

202= 400 dipeptides

Page 24: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

203 = 8000 tripeptide

20100= 1.3 x 10130

Page 25: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Oligopeptide = short to medium-length aa chain (5 to100 aa’s) fuzzy borders

 

Polypeptide = over 100 aa’s in the chain

Page 26: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

A thiol (same family as O)

Can form disulfide bonds

Page 27: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 28: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 29: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 30: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Strong covalent bonds

Page 31: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 32: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Weak, but plentiful H bondse.g. wool

Page 33: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Not as stretchy: e.g. silk

Page 34: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 35: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 36: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Proteins play many roles in cells: 

• structural (e.g. collagen in connective tissue)

• movement (e.g. actin & myosin in muscles)

• transport (e.g. hemoglobin, LDL, HDL)

• catalysis (e.g. wide variety of enzymes)

• regulation (e.g. hormones such as insulin)

Page 37: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Nucleic acids: energy and genetics

Page 38: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

BASE vs.

NUCLEOSIDE (base + sugar) vs.

NUCLEOTIDE (base + sugar + phosphate)

Page 39: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 40: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 41: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

RNA’s base

Page 42: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

DNA vs RNA structure

Page 43: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 44: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Composed of nucleotide monomers:A 5 C sugar, a phosphate,

and nitrogenous bases:

Page 45: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 46: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 47: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 48: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler
Page 49: Organic Chem: Biochemistry. Biochemistry Study of chem of living organisms Most: large, complex molecules complex molecules: biopolymers  smaller, simpler

Watson & Crick back in the 1950’s

Modern genetic engineering

Rosalind Franklin