3. Above is a relative of S-adenosylmethionine (SAM) called S-adenosvlmethionineamine (while there is no common abbreviation for this molecule, here we can call it SAMN). Note that R'-S-R is a very good leaving group. You do not need to know anything else about sulfur to answer this question. It is recommended to work this problem after Problem 2, keeping in mind the three circled carbon atoms from Problem 2. To save excessive writing, you may abbreviate adenosine as "Ado" as shown in the pathway diagram below. a) b) SAMN can serve as more than a methylating agent. Do you think that its intrinsic chemical activity as a methylating agent is substantially more, similar to, or less than SAM? SAMN is used in biochemistry in the below pathway, which converts the stinky diamine putrescine into the "polyamine" spermine which is used biologically for offsetting the negative charges in DNA. Draw spermine in its most common protonation state at pH 7. c) Draw the reaction of putrescine with SAMN (shown as with the adenosine abbreviated as "Ado" in the below diagram) to form spermidine using the arrow formalism. putrescine H₂N- H₂N spermidine synthase H₂N spermine synthase NH₂ H₂N. S-Ado NH₂ spermidine NH₂ spermine

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter27: Amines
Section: Chapter Questions
Problem 14E
icon
Related questions
icon
Concept explainers
Question
3. Above is a relative of S-adenosylmethionine (SAM) called S-adenosvlnethionineamine (while there is
no common abbreviation for this molecule, here we can call it SAMN). Note that R'-S-R is a very good
leaving group. You do not need to know anything else about sulfur to answer this question. It is
recommended to work this problem after Problem 2, keeping in mind the three circled carbon atoms
from Problem 2. To save excessive writing, you may abbreviate adenosine as "Ado" as shown in the
pathway diagram below.
a) SAMN can serve as more than a methylating agent. Do you think that its intrinsic chemical
activity as a methylating agent is substantially more, șimilar to, or less than SAM?
b) SAMN is used in biochemistry in the below pathway, which converts the stinky diamine
putrescine into the "polyamine" spermine which is used biologically for offsetting the
negative charges in DNA. Draw spermine in its most common protonation state at pH 7.
c) Draw the reaction of putrescine with SAMN (shown as with the adenosine abbreviated as
"Ado" in the below diagram) to form spermidine using the arrow formalism.
H2N.
putrescine
`NH2
H2N.
spermidine
synthase
`Ado
`Ado
HN.
`NH2
spermidine
spermine
synthase
H2N.
`NH, spermine
d) Would the reaction to form spermidine tend to occur more rapidly at pH 5 or pH 9?
e) A similar reaction can yield spermine. Draw this reaction.
Transcribed Image Text:3. Above is a relative of S-adenosylmethionine (SAM) called S-adenosvlnethionineamine (while there is no common abbreviation for this molecule, here we can call it SAMN). Note that R'-S-R is a very good leaving group. You do not need to know anything else about sulfur to answer this question. It is recommended to work this problem after Problem 2, keeping in mind the three circled carbon atoms from Problem 2. To save excessive writing, you may abbreviate adenosine as "Ado" as shown in the pathway diagram below. a) SAMN can serve as more than a methylating agent. Do you think that its intrinsic chemical activity as a methylating agent is substantially more, șimilar to, or less than SAM? b) SAMN is used in biochemistry in the below pathway, which converts the stinky diamine putrescine into the "polyamine" spermine which is used biologically for offsetting the negative charges in DNA. Draw spermine in its most common protonation state at pH 7. c) Draw the reaction of putrescine with SAMN (shown as with the adenosine abbreviated as "Ado" in the below diagram) to form spermidine using the arrow formalism. H2N. putrescine `NH2 H2N. spermidine synthase `Ado `Ado HN. `NH2 spermidine spermine synthase H2N. `NH, spermine d) Would the reaction to form spermidine tend to occur more rapidly at pH 5 or pH 9? e) A similar reaction can yield spermine. Draw this reaction.
Expert Solution
steps

Step by step

Solved in 6 steps

Blurred answer
Knowledge Booster
Electronic Effects
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning