December 22, 2024, 04:24:18 PM
Forum Rules: Read This Before Posting


Topic: Glutamate arginine  (Read 3392 times)

0 Members and 1 Guest are viewing this topic.

Offline orgo814

  • Full Member
  • ****
  • Posts: 412
  • Mole Snacks: +11/-6
Glutamate arginine
« on: September 07, 2014, 08:22:01 PM »
How is glutamate a precursor for arginine? Have been scratching my head about this mainly because of that extra CH2 group arg has. Any insight appreciated

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 5716
  • Mole Snacks: +331/-24
Re: Glutamate arginine
« Reply #1 on: September 08, 2014, 10:41:04 AM »
Suppose that you were able to protect the amino nitrogen and then reduce this derivative of glutamate at C-1.  What could happen next?

Offline orgo814

  • Full Member
  • ****
  • Posts: 412
  • Mole Snacks: +11/-6
Re: Glutamate arginine
« Reply #2 on: September 08, 2014, 02:51:20 PM »
Not sure what you mean. Protect amino?

Offline kriggy

  • Chemist
  • Sr. Member
  • *
  • Posts: 1520
  • Mole Snacks: +136/-16
Re: Glutamate arginine
« Reply #3 on: September 08, 2014, 05:05:19 PM »
Suppose that you were able to protect the amino nitrogen and then reduce this derivative of glutamate at C-1.  What could happen next?

Protect so it doesnt form cyclic product?

Not sure what you mean. Protect amino?
http://en.wikipedia.org/wiki/Protecting_group

Might help understand what is ment by protecting.
its not that the arginine is formed in single step, its more of reaction sequence with several intermediates

Offline Babcock_Hall

  • Chemist
  • Sr. Member
  • *
  • Posts: 5716
  • Mole Snacks: +331/-24
Re: Glutamate arginine
« Reply #4 on: September 08, 2014, 07:47:36 PM »
butlerw2,

The biosynthesis of arginine from glutamate is indeed a multistep pathway.  In the first step, glutamate is converted to N-acetylglutamate, and the acetyl group is removed at the end of the biosynthesis.  The textbook explanation of why the acetylation takes place is to prevent an unwanted side-reaction (cyclization) once the gamma-carboxylate group is reduced to an aldehyde.  Offhand, this is the only example I can think of where nature uses protecting group chemistry, but there must be others.

Sponsored Links