Class Notes (1,100,000)
CA (620,000)
UBC (10,000)
BIOC (100)
Lecture 1

BIOC 302 Lecture Notes - Lecture 1: Anomer, Pentose, Enol


Department
Biochemistry
Course Code
BIOC 302
Professor
Michael J.Krisinger
Lecture
1

This preview shows half of the first page. to view the full 1 pages of the document.
ฮฒ-N-glycosidic link
Alkene
Aroma๎€”c ring planar
Tautomeriza๎€Žon Lone pair
nitrogen and keto group
keto goes to enol
5โ€™ is di๎€›erent than
the other 4 achiral
Secondary alcohol
(also in 3โ€™)
In PowderIn Aqueous Solโ€™n
Lecture 1 โ€“ Feb 22/16
DNA
transcription
โ†’
RNA
translation
โ†’
Proteins
Nucleic Acids
-Prime is used to dis๎€”nguish between the purine/pyrimidine ring and the pentose ring.
-1โ€™ carbon = the anomeric carbon โ€“ links the chains together
-Bond between carbohydrates = glycosidic bond
oฮฒ-N-glycosidic bond โ€“ the link that is always between all nucleic
acids ๏ƒ  the bond goes โ€œup/out of the pageโ€
-Reac๎€”on required to make the bond between the pentose and the
purine/pyrimidine = condensa๎€Žon
-Phosphate bond: pKa = ~1 ๏ƒ  nega๎€”ve under physiological condi๎€”ons
Nucelo๎€”des: Sugars
-The sugar in ribonucelosides is D-ribose
oNucleoside ๏ƒ  no phosphate
oNucleo๎€”de ๏ƒ  phosphate
-The sugar in deoxyribonucleosides is a deriva๎€”ve of this: 2-deoxy-D-ribose (no hydroxyl group in the 2โ€™ posi๎€”on)
-To switch from linear to ring form, you form an ether (alcohol ๏ƒ  ether)
oketone ๏ƒ  alcohol
oaldehyde + alcohol ๏ƒ  hemi-acetal
-Furan is NOT similar to furanose.
Feb 22 Ques๎€‰on of the day: hydrolysis of the N-glycosyl bond between the
deoxyribose and a purine in DNA creates an AP site (no base โ€“ at the 1โ€™ carbon,
there is an OH group). Examine the structure of an AP site and describe chemical
consequences of such base loss.
-The ring can break open and become linear ๏ƒ  aldehydes are rather
reac๎€”ve = cytotoxic
replica๎€‰on
You're Reading a Preview

Unlock to view full version