Organic Chemistry-Access
9th Edition
ISBN: 9781305671201
Author: McMurry
Publisher: Cengage
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 25.SE, Problem 31MP
Interpretation Introduction
Interpretation:
To propose a mechanism of mannose 6-phosphate derivative from fructose 6-phosphate.
Concept introduction:
Acid-base Catalysis by the enzyme.
Step 1: Substrate binding.
Step 2: Acid catalyzed ring opening.
Step 3: Base abstracts the acidic proton from C2 to form a cis enediolete intermediate.
Step 4: proten is replaced on C-1 as ab iverall proton teamster.
Step 5: Ring disuse to form product.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Draw the product of the mutarotation of the monosaccharide
shown below.
ОҢ
CH₂OH
ОН
ОН
H3O+
OH
6
m) Which pyranose ring (A, B, C, or D) in the tetrasaccharide below is derived from D-altrose? The Fischer
projections for the four aldohexoses that make up this tetrasaccharide are shown below.
B
C
D
HOH
CHO
CHO
CHO
CHO
HO+H HTOH Fонно н
HOH HOH H-OH H-OH
H-+-OH H-TOHHOH HOH
H+OH HOHнтон нон
CHOH CHOH CHOH CHOH
De D-glue Dalose Datrone
i
NH
Į
HOH
STEP 1
OH, HO-
answer
1. Just add arrows and charges for steps 1, 2, and 3 in formation of this enamine
з
no arrows
needed
here
OH н
Н
ЮН
-OH
STEP 3
:ÖH
н
H
STEP 2
на это про за поч
Name the monosaccharides in the images by placing the appropriate terms.
HO-
H
OH
|- |-galacto
000
Incorrect
CH₂OH
OH
00000
CH₂OH
aldopentose
aldotetrose
ketotetrose
aldotriose
Oketopentose
Oketotriose
fructose
CHO
-H
-OH
O OH
aldohexose
Oketopentose
Ⓒaldotetrose
OH
aldopentose
ketohexose
OHT
B furanose
OH
0- --gluco
CH,OH
Answer Bank
D
Classify each monosaccharide according to the position of the carbonyi group and the number of cards
the molecule.
L
OH
pyranose
OH
00000
CH₂OH
OLI
Incorrect
OIL
OH
ketohexose
aldohexose
ketotetrose
aldopentose
Oaldotetrose
ketopentose
a
OH
CH₂OH OH
O
HO
OH
-fructo
CH₂OH
CS CamScanner
Chapter 25 Solutions
Organic Chemistry-Access
Ch. 25.1 - Prob. 1PCh. 25.2 - Prob. 2PCh. 25.2 - Prob. 3PCh. 25.2 - Prob. 4PCh. 25.2 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.4 - Prob. 8PCh. 25.4 - Prob. 9PCh. 25.4 - Prob. 10P
Ch. 25.5 - Prob. 11PCh. 25.5 - Prob. 12PCh. 25.5 - Prob. 13PCh. 25.5 - Prob. 14PCh. 25.5 - Prob. 15PCh. 25.6 - Prob. 16PCh. 25.6 - Prob. 17PCh. 25.6 - Prob. 18PCh. 25.6 - Prob. 19PCh. 25.6 - Prob. 20PCh. 25.6 - Prob. 21PCh. 25.6 - Prob. 22PCh. 25.6 - Prob. 23PCh. 25.7 - Prob. 24PCh. 25.8 - Show the product you would obtain from the...Ch. 25.SE - Prob. 26VCCh. 25.SE - Prob. 27VCCh. 25.SE - Prob. 28VCCh. 25.SE - Prob. 29VCCh. 25.SE - Prob. 30MPCh. 25.SE - Prob. 31MPCh. 25.SE - Glucosamine, one of the eight essential...Ch. 25.SE - D-Glicose reacts with acetone in the presence of...Ch. 25.SE - Prob. 34MPCh. 25.SE - Prob. 35MPCh. 25.SE - Prob. 36APCh. 25.SE - Prob. 37APCh. 25.SE - Prob. 38APCh. 25.SE - Prob. 39APCh. 25.SE - Prob. 40APCh. 25.SE - Assign R or S configuration to each chirality...Ch. 25.SE - Prob. 42APCh. 25.SE - Prob. 43APCh. 25.SE - Prob. 44APCh. 25.SE - Prob. 45APCh. 25.SE - Prob. 46APCh. 25.SE - Prob. 47APCh. 25.SE - Prob. 48APCh. 25.SE - Prob. 49APCh. 25.SE - Prob. 50APCh. 25.SE - Prob. 51APCh. 25.SE - Prob. 52APCh. 25.SE - Prob. 53APCh. 25.SE - Prob. 54APCh. 25.SE - Prob. 55APCh. 25.SE - Prob. 56APCh. 25.SE - Prob. 57APCh. 25.SE - Prob. 58APCh. 25.SE - Prob. 59APCh. 25.SE - Prob. 60APCh. 25.SE - Prob. 61APCh. 25.SE - Prob. 62APCh. 25.SE - Prob. 63APCh. 25.SE - D-Mannose reacts with acetone to give a...Ch. 25.SE - Prob. 65APCh. 25.SE - Prob. 66APCh. 25.SE - Prob. 67APCh. 25.SE - Prob. 68APCh. 25.SE - Prob. 69APCh. 25.SE - Prob. 70APCh. 25.SE - Prob. 71AP
Knowledge Booster
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
- 1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose. 2. Consider the structure of the disaccharide drawn at right: НО `CH2 В ОН (a) Give the names and D/L designation for the two monosaccharides linked together. H,C-O OHO „OH OH А: НО НО A В: ОН (b) In the structure, circle the anomeric carbon of each saccharide. (c) Is each saccharide present in its a or ß anomer? Specify both A and B (d) Would this disaccharide undergo mutarotation? Why or why not? (e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why not? (f) There are two reasons this is very unlikely to be a naturally occurring disaccharide. What about its structure suggests this is true? Give both reasons.arrow_forwardНО Но н Н- НО он Н Н HO H OH оно н Н H. H Н ОН Н H н 아처 OH CH НО.arrow_forwardN-NHPH CHO CH2OH H- C=N-NHPH Но- -H- 3 equiv Но- -H- 3 equiv Но- PHNHNH2 PHNHNH, H- H- OH H- -O- H- H- -HO- H- -HO- ČH2OH ČH2OH ČH2OH D-glucose osazone D-fructose + NH3 + PHNH2 + 2 H20 The final step in the formation of the osazone from glucose is the reaction of the keto imine with 2 equivalents of phenylhydrazine to yield the osazone plus ammonia. This reaction involves the following intermediate steps: 1. Addition of phenylhydrazine to the imine and proton transfer to yield intermediate 1; 2. Elimination of ammonia to yield phenylhydrazone 2; 3. Addition of phenylhydrazine to the ketone to yield tetrahedral intermediate 3; 4. Proton transfer yields carbinolamine 4; 5. Elimination of water yields the final product osazone. Write out the mechanism on a separate sh of paper and then draw the structure of tetrahedral intermediate 3. NH НО- -H H- -ОН H- -ОН ОН Glucose keto imine Previous Nearrow_forward
- (d) Draw the structure of the expected product when monosaccharide B undergo mutarotation upon dissolving in water in the presence of Tollens reagent (AGNO3, NHẠOH). он OH O. OH OH OH monosaccharide Barrow_forwardThe following sugar is? -ОН Но ОН O Но 0 ОН O A reducing sugar O Linked by an N-glycosidic bond O Derived from 2 ketoses O A non-reducing sugar trisaccharide -ОН НО ОНarrow_forwardDraw the product of the mutarotation of the monosaccharide shown below. ОН CH₂OH ОН ОН H3O+ ОН of вarrow_forward
- a) Which of the following polysaccharides is a segment of amylose? CH2OH CH2OH CH2OH CH2OH OH OH OH OH ОН H H H OH OH OH ОН Structure I CH2OH CH2OH CH2OH CH2OH OH ОН OH ОН OH OH ОН OH Structure II b) Which one is a segment of cellulose? CH2OH CH2OH CH2OH CH2OH ОН OH OH ОН ОН OH ОН ОН ОН Structure I CH2OH CH2OH CH2OH CH2OH O. ОН ОН OH ОН OH OH OH OH Structure IIarrow_forward4. Identify the component monosaccharides of each of the following compounds and describe the type of glycosidic linkage in each. Но он Но OH HO он Но- Но- (a) OH (c) CH,OHO. (b) CH2OHO Lon OH HO H ČHOH H OH ÓH ОНarrow_forwarda) Which of the following monosaccharides will react with Tollens' reagent? Circle all that apply. СООН CH2OH CH2OH OCH3 но- H- O: OH но H- но—н OH ČH2OH ČH2OH ÓH II III IV V b) Which of the following carbohydrates is sucrose? OH OH OH но OH HO, O. OH "OH HO OH Он HO OH II I HO, HO. Он HO, HO. HO, OH Но Он но. OH HO,, HO, OH HOl HO OH но он III Он HO IV HO ноarrow_forward
- Shown here is a/anglycosidic linkage. CH₂OH CH₂OH I OH Н OH Н O Alpha Beta OL- O D- О Н I ОН HO OH -О Н Н H OH OHarrow_forward3. Propose a mechanism for the conversion from ribulose5-5phosphate to ribose-5-phosphate using the arrow formalism. This is a reaction in the pentose phosphate pathway. CH2OH с-н Ribose 5-Phosphate Isomerase c=0 H-C-OH Н-с-ОН Н-с-ОН Н-с-он Н-с-ОН H2C-OPO,2 H2C-OPO, Ribulose-5-Phosphate Ribose-5-Phosphatearrow_forwardRaffinose is a trisaccharide (C18H32O16) isolated from cottonseed meal. Raffinose doesnot reduce Tollens reagent, and it does not mutarotate. Complete hydrolysis of raffinosegives d-glucose, d-fructose, and d-galactose. When raffinose is treated with invertase,the products are d-fructose and a reducing disaccharide called melibiose. Raffinose isunaffected by treatment with a b@galactosidase, but an a@galactosidase hydrolyzes itto d-galactose and sucrose. When raffinose is treated with dimethyl sulfate and basefollowed by hydrolysis, the products are 2,3,4-tri-O-methylglucose, 1,3,4,6-tetraO-methylfructose, and 2,3,4,6-tetra-O-methylgalactose. Determine the completestructures of raffinose and melibiose, and give a systematic name for melibiose.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning