Methionine can react with ATP to generate S-adenylmethionine (SAM). NH2 N но. NH2 но-р-о-р-о-р-о он Он но NN OH OH methionine АТР step 1 NH2 NH2 + HO. %3D + но-р-о-р-о-р-он Он OH OH но N. Он SAM triphosphate step 2 NH2 но. NH2 + но-Р-о-Р-он + но-р-он ÓH OH OH но OH N он pyrophosphate orthophosphate (D) Draw methionine in all lone pair electrons and indicate the hybridization for each carbon, oxygen, and nitrogen. (E) Step 1 at SAM synthesis proceeds by an SN2 mechanism. Draw the reaction mechanism using the arrow formalism. (F) Justify why this reaction proceeds via SN2 rather than SN1 mechanism.

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
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Chapter29: The Organic Chemistry Of Metabolic Pathways
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Problem 24MP: One of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of xylulose...
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Methionine can react with ATP to generate S-adenylmethionine (SAM).
NH2
„NH2
но.
+ HO-P-o-P-o-P-o
но-
OH
Он
он
но
он
methionine
ATP
step 1
NH,
N:
ZHN
+
но
но-р-о-р-о-р-он
ÓH
OH
ÓH
OH
SAM
triphosphate
step 2
NH2
Но.
NH2
+ но-р-о-р- он + но-р-он
OH
ÓH
OH
но
N.
OH
pyrophosphate
orthophosphate
(D) Draw methionine in all lone pair electrons and indicate the hybridization for each carbon,
oxygen, and nitrogen.
(E) Step 1 at SAM synthesis proceeds by an SN2 mechanism. Draw the reaction mechanism using
the arrow formalism.
(F) Justify why this reaction proceeds via SN2 rather than SN1 mechanism.
(G) Draw the mechanism for step 2 using the arrow formalism.
(H) Which step (1 or 2) is more thermodynamically favorable? Briefly justify your answer.
(1) Draw the reaction of glycine with SAM to generate N-methyl-glycine (this metabolite is common
enough to have its own name, sarcosine, and as a negative predictor of outcome in prostate
cancer). What is the reaction mechanism?
Transcribed Image Text:Methionine can react with ATP to generate S-adenylmethionine (SAM). NH2 „NH2 но. + HO-P-o-P-o-P-o но- OH Он он но он methionine ATP step 1 NH, N: ZHN + но но-р-о-р-о-р-он ÓH OH ÓH OH SAM triphosphate step 2 NH2 Но. NH2 + но-р-о-р- он + но-р-он OH ÓH OH но N. OH pyrophosphate orthophosphate (D) Draw methionine in all lone pair electrons and indicate the hybridization for each carbon, oxygen, and nitrogen. (E) Step 1 at SAM synthesis proceeds by an SN2 mechanism. Draw the reaction mechanism using the arrow formalism. (F) Justify why this reaction proceeds via SN2 rather than SN1 mechanism. (G) Draw the mechanism for step 2 using the arrow formalism. (H) Which step (1 or 2) is more thermodynamically favorable? Briefly justify your answer. (1) Draw the reaction of glycine with SAM to generate N-methyl-glycine (this metabolite is common enough to have its own name, sarcosine, and as a negative predictor of outcome in prostate cancer). What is the reaction mechanism?
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