How are glycosidic linkages formed?How do we assign alpha/beta status in polysaccharides?How is it that fructose has a different metabolic pathway than glucose but yet glucose is converted to fructose?How to Convert Sucrose to Glucose and FructoseWhy are glycosidic bonds always 1->4 in polysaccharides?Differentiating esters from glycosidic linkagesAre β-sheets formed from one or more polypeptides?Hydrolysis of β-1,2 glycosidic bondHow does existence of alpha and beta form of glucose prove that it exists as a cyclic structure
What is the following style of typography called?
Cutting a 4.5m long 2x6 in half with a circular saw
When and why did the House rules change to permit an inquiry without a vote?
Could you use uppercase or special characters in a password in early Unix?
Are there any Baryons that have quark-antiquark combinations?
What's the meaning of Electrical Inches?
Why doesn't hot charcoal glow blue?
Is it really better for the environment if I take the stairs as opposed to a lift?
when to use がつ or げつ readings for 月？
Rules on "Pets on shoulder"
Linux Commands in Python
Why is 10.1.255.255 an invalid broadcast address?
Is there any research on the development of attacks against artificial intelligence systems?
What exactly is meant by "partial function" in functional programming?
Why were germanium diodes so fast and germanium transistors so slow?
Most optimal hallways with random gravity inside?
What would a chair for a Human with a Tail look like?
Why is this a missed win?
Why are Krueger flaps called flaps and not slats?
Is the phrase “You are requested” polite or rude?
To project, or not to project? Extracting raster values with R
Does code obfuscation give any measurable security benefit?
Have the US and Russia (or USSR before it) co-vetoed a UN resolution before today?
How does an Evocation Wizard's Overchannel ability interact with Chaos Bolt?
How are glycosidic linkages formed?
How do we assign alpha/beta status in polysaccharides?How is it that fructose has a different metabolic pathway than glucose but yet glucose is converted to fructose?How to Convert Sucrose to Glucose and FructoseWhy are glycosidic bonds always 1->4 in polysaccharides?Differentiating esters from glycosidic linkagesAre β-sheets formed from one or more polypeptides?Hydrolysis of β-1,2 glycosidic bondHow does existence of alpha and beta form of glucose prove that it exists as a cyclic structure
.everyoneloves__top-leaderboard:empty,.everyoneloves__mid-leaderboard:empty,.everyoneloves__bot-mid-leaderboard:empty
margin-bottom:0;
$begingroup$
Consider glycosidic linkages in disaccharides.
I know a condensation reaction occurs, with the loss of water.
But which OH is lost? The O in the linkage belongs to which monosaccharide?
Example: take sucrose, the O in the linkage belongs to fructose or glucose?
I couldn't find any literature regarding this. Any help is appreciated .
biochemistry chemical-biology carbohydrates
asked May 26 at 5:52
user226375user226375
3508 bronze badges
$endgroup$
add a comment
|
$begingroup$
Consider glycosidic linkages in disaccharides.
I know a condensation reaction occurs, with the loss of water.
But which OH is lost? The O in the linkage belongs to which monosaccharide?
Example: take sucrose, the O in the linkage belongs to fructose or glucose?
I couldn't find any literature regarding this. Any help is appreciated .
biochemistry chemical-biology carbohydrates
asked May 26 at 5:52
user226375user226375
3508 bronze badges
$endgroup$
add a comment
|
$begingroup$
Consider glycosidic linkages in disaccharides.
I know a condensation reaction occurs, with the loss of water.
But which OH is lost? The O in the linkage belongs to which monosaccharide?
Example: take sucrose, the O in the linkage belongs to fructose or glucose?
I couldn't find any literature regarding this. Any help is appreciated .
biochemistry chemical-biology carbohydrates
asked May 26 at 5:52
user226375user226375
3508 bronze badges
$endgroup$
Consider glycosidic linkages in disaccharides.
I know a condensation reaction occurs, with the loss of water.
But which OH is lost? The O in the linkage belongs to which monosaccharide?
Example: take sucrose, the O in the linkage belongs to fructose or glucose?
I couldn't find any literature regarding this. Any help is appreciated .
biochemistry chemical-biology carbohydrates
biochemistry chemical-biology carbohydrates
asked May 26 at 5:52
user226375user226375
3508 bronze badges
asked May 26 at 5:52
user226375user226375
3508 bronze badges
asked May 26 at 5:52
user226375user226375
3508 bronze badges
asked May 26 at 5:52
user226375user226375
3508 bronze badges
asked May 26 at 5:52
user226375user226375
3508 bronze badges
3508 bronze badges
add a comment
|
add a comment
|
1 Answer
1
active
oldest
votes
$begingroup$
In sucrose molecule the glycosidic linkage is formed by the OH group on the anomeric carbon of α-D-glucose and the OH group on the anomeric carbon of β-D-fructose.
source :
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(McMurry)/Chapter_25%3A_Biomolecules%3A_Carbohydrates/25.08_Disaccharides
As seen, in either alpha d-glucose or beta d-fructo furanose may react to give sucrose.
Let us examin.
Alpha D-gluco Pyranose gives an intermediate 1 and 2 by protonation at anomeric carbon.
Similarly Beta D-fructo furanose gives an intermediate 3 and 4 by protonation at anomeric carbon.
If you examine , structure 3 is more stable then structure 4.
The negative inductive effect of CH2OH in fructofuranose destablizes this intermediate 4.
Hence structure 2 , an intermediate of aplha D-gluco pyranose (more stable) attacks beta D-fructo furanose togive sucrose.
The above diagrams are author drawn in CHEM DRAW
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0321 gold badge5 silver badges25 bronze badges
$endgroup$
1
$begingroup$
This entire answer appears to be copy-pasted from Bruice's Organic chemistry. If you are quoting third-party sources, or using any graphics/data/plots that are not made by you, put an appropriate reference and denote the part that is quoted with proper markup (>). Keep in mind that if you don't that you may eventually be accused of plagiarism.
$endgroup$
– andselisk♦
May 26 at 7:23
$begingroup$
@user226375 your question is answered now,
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:42
$begingroup$
@andselisk you were correect .This was taken from Bruice's Organic chemistry.(missed reference ).How ever the answer is rewritten ti the question asked .The diagrams are mine , drawn on CHEMDRAW.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:44
2
$begingroup$
@andselisk I MISSED QUOTING REFERENECE IN HURRY TO ANSWER .MY APOLOGIES .THIS WAS NOT DONE ON PURPOUSE.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:52
add a comment
|
Your Answer
StackExchange.ready(function()
var channelOptions =
tags: "".split(" "),
id: "431"
;
initTagRenderer("".split(" "), "".split(" "), channelOptions);
StackExchange.using("externalEditor", function()
// Have to fire editor after snippets, if snippets enabled
if (StackExchange.settings.snippets.snippetsEnabled)
StackExchange.using("snippets", function()
createEditor();
);
else
createEditor();
);
function createEditor()
StackExchange.prepareEditor(
heartbeatType: 'answer',
autoActivateHeartbeat: false,
convertImagesToLinks: false,
noModals: true,
showLowRepImageUploadWarning: true,
reputationToPostImages: null,
bindNavPrevention: true,
postfix: "",
imageUploader:
brandingHtml: "Powered by u003ca class="icon-imgur-white" href="https://imgur.com/"u003eu003c/au003e",
contentPolicyHtml: "User contributions licensed under u003ca href="https://creativecommons.org/licenses/by-sa/4.0/"u003ecc by-sa 4.0 with attribution requiredu003c/au003e u003ca href="https://stackoverflow.com/legal/content-policy"u003e(content policy)u003c/au003e",
allowUrls: true
,
onDemand: true,
discardSelector: ".discard-answer"
,immediatelyShowMarkdownHelp:true
);
);
Sign up or log in
StackExchange.ready(function ()
StackExchange.helpers.onClickDraftSave('#login-link');
);
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
StackExchange.ready(
function ()
StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fchemistry.stackexchange.com%2fquestions%2f115942%2fhow-are-glycosidic-linkages-formed%23new-answer', 'question_page');
);
Post as a guest
Required, but never shown
1 Answer
1
active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
$begingroup$
In sucrose molecule the glycosidic linkage is formed by the OH group on the anomeric carbon of α-D-glucose and the OH group on the anomeric carbon of β-D-fructose.
source :
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(McMurry)/Chapter_25%3A_Biomolecules%3A_Carbohydrates/25.08_Disaccharides
As seen, in either alpha d-glucose or beta d-fructo furanose may react to give sucrose.
Let us examin.
Alpha D-gluco Pyranose gives an intermediate 1 and 2 by protonation at anomeric carbon.
Similarly Beta D-fructo furanose gives an intermediate 3 and 4 by protonation at anomeric carbon.
If you examine , structure 3 is more stable then structure 4.
The negative inductive effect of CH2OH in fructofuranose destablizes this intermediate 4.
Hence structure 2 , an intermediate of aplha D-gluco pyranose (more stable) attacks beta D-fructo furanose togive sucrose.
The above diagrams are author drawn in CHEM DRAW
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0321 gold badge5 silver badges25 bronze badges
$endgroup$
1
$begingroup$
This entire answer appears to be copy-pasted from Bruice's Organic chemistry. If you are quoting third-party sources, or using any graphics/data/plots that are not made by you, put an appropriate reference and denote the part that is quoted with proper markup (>). Keep in mind that if you don't that you may eventually be accused of plagiarism.
$endgroup$
– andselisk♦
May 26 at 7:23
$begingroup$
@user226375 your question is answered now,
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:42
$begingroup$
@andselisk you were correect .This was taken from Bruice's Organic chemistry.(missed reference ).How ever the answer is rewritten ti the question asked .The diagrams are mine , drawn on CHEMDRAW.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:44
2
$begingroup$
@andselisk I MISSED QUOTING REFERENECE IN HURRY TO ANSWER .MY APOLOGIES .THIS WAS NOT DONE ON PURPOUSE.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:52
add a comment
|
$begingroup$
In sucrose molecule the glycosidic linkage is formed by the OH group on the anomeric carbon of α-D-glucose and the OH group on the anomeric carbon of β-D-fructose.
source :
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(McMurry)/Chapter_25%3A_Biomolecules%3A_Carbohydrates/25.08_Disaccharides
As seen, in either alpha d-glucose or beta d-fructo furanose may react to give sucrose.
Let us examin.
Alpha D-gluco Pyranose gives an intermediate 1 and 2 by protonation at anomeric carbon.
Similarly Beta D-fructo furanose gives an intermediate 3 and 4 by protonation at anomeric carbon.
If you examine , structure 3 is more stable then structure 4.
The negative inductive effect of CH2OH in fructofuranose destablizes this intermediate 4.
Hence structure 2 , an intermediate of aplha D-gluco pyranose (more stable) attacks beta D-fructo furanose togive sucrose.
The above diagrams are author drawn in CHEM DRAW
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0321 gold badge5 silver badges25 bronze badges
$endgroup$
1
$begingroup$
This entire answer appears to be copy-pasted from Bruice's Organic chemistry. If you are quoting third-party sources, or using any graphics/data/plots that are not made by you, put an appropriate reference and denote the part that is quoted with proper markup (>). Keep in mind that if you don't that you may eventually be accused of plagiarism.
$endgroup$
– andselisk♦
May 26 at 7:23
$begingroup$
@user226375 your question is answered now,
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:42
$begingroup$
@andselisk you were correect .This was taken from Bruice's Organic chemistry.(missed reference ).How ever the answer is rewritten ti the question asked .The diagrams are mine , drawn on CHEMDRAW.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:44
2
$begingroup$
@andselisk I MISSED QUOTING REFERENECE IN HURRY TO ANSWER .MY APOLOGIES .THIS WAS NOT DONE ON PURPOUSE.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:52
add a comment
|
$begingroup$
In sucrose molecule the glycosidic linkage is formed by the OH group on the anomeric carbon of α-D-glucose and the OH group on the anomeric carbon of β-D-fructose.
source :
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(McMurry)/Chapter_25%3A_Biomolecules%3A_Carbohydrates/25.08_Disaccharides
As seen, in either alpha d-glucose or beta d-fructo furanose may react to give sucrose.
Let us examin.
Alpha D-gluco Pyranose gives an intermediate 1 and 2 by protonation at anomeric carbon.
Similarly Beta D-fructo furanose gives an intermediate 3 and 4 by protonation at anomeric carbon.
If you examine , structure 3 is more stable then structure 4.
The negative inductive effect of CH2OH in fructofuranose destablizes this intermediate 4.
Hence structure 2 , an intermediate of aplha D-gluco pyranose (more stable) attacks beta D-fructo furanose togive sucrose.
The above diagrams are author drawn in CHEM DRAW
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0321 gold badge5 silver badges25 bronze badges
$endgroup$
In sucrose molecule the glycosidic linkage is formed by the OH group on the anomeric carbon of α-D-glucose and the OH group on the anomeric carbon of β-D-fructose.
source :
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Map%3A_Organic_Chemistry_(McMurry)/Chapter_25%3A_Biomolecules%3A_Carbohydrates/25.08_Disaccharides
As seen, in either alpha d-glucose or beta d-fructo furanose may react to give sucrose.
Let us examin.
Alpha D-gluco Pyranose gives an intermediate 1 and 2 by protonation at anomeric carbon.
Similarly Beta D-fructo furanose gives an intermediate 3 and 4 by protonation at anomeric carbon.
If you examine , structure 3 is more stable then structure 4.
The negative inductive effect of CH2OH in fructofuranose destablizes this intermediate 4.
Hence structure 2 , an intermediate of aplha D-gluco pyranose (more stable) attacks beta D-fructo furanose togive sucrose.
The above diagrams are author drawn in CHEM DRAW
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0321 gold badge5 silver badges25 bronze badges
edited May 26 at 8:47
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0321 gold badge5 silver badges25 bronze badges
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0321 gold badge5 silver badges25 bronze badges
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0321 gold badge5 silver badges25 bronze badges
3,0321 gold badge5 silver badges25 bronze badges
1
$begingroup$
This entire answer appears to be copy-pasted from Bruice's Organic chemistry. If you are quoting third-party sources, or using any graphics/data/plots that are not made by you, put an appropriate reference and denote the part that is quoted with proper markup (>). Keep in mind that if you don't that you may eventually be accused of plagiarism.
$endgroup$
– andselisk♦
May 26 at 7:23
$begingroup$
@user226375 your question is answered now,
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:42
$begingroup$
@andselisk you were correect .This was taken from Bruice's Organic chemistry.(missed reference ).How ever the answer is rewritten ti the question asked .The diagrams are mine , drawn on CHEMDRAW.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:44
2
$begingroup$
@andselisk I MISSED QUOTING REFERENECE IN HURRY TO ANSWER .MY APOLOGIES .THIS WAS NOT DONE ON PURPOUSE.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:52
add a comment
|
1
$begingroup$
This entire answer appears to be copy-pasted from Bruice's Organic chemistry. If you are quoting third-party sources, or using any graphics/data/plots that are not made by you, put an appropriate reference and denote the part that is quoted with proper markup (>). Keep in mind that if you don't that you may eventually be accused of plagiarism.
$endgroup$
– andselisk♦
May 26 at 7:23
$begingroup$
@user226375 your question is answered now,
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:42
$begingroup$
@andselisk you were correect .This was taken from Bruice's Organic chemistry.(missed reference ).How ever the answer is rewritten ti the question asked .The diagrams are mine , drawn on CHEMDRAW.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:44
2
$begingroup$
@andselisk I MISSED QUOTING REFERENECE IN HURRY TO ANSWER .MY APOLOGIES .THIS WAS NOT DONE ON PURPOUSE.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:52
1
1
$begingroup$
This entire answer appears to be copy-pasted from Bruice's Organic chemistry. If you are quoting third-party sources, or using any graphics/data/plots that are not made by you, put an appropriate reference and denote the part that is quoted with proper markup (
>). Keep in mind that if you don't that you may eventually be accused of plagiarism.$endgroup$
– andselisk♦
May 26 at 7:23
$begingroup$
This entire answer appears to be copy-pasted from Bruice's Organic chemistry. If you are quoting third-party sources, or using any graphics/data/plots that are not made by you, put an appropriate reference and denote the part that is quoted with proper markup (
>). Keep in mind that if you don't that you may eventually be accused of plagiarism.$endgroup$
– andselisk♦
May 26 at 7:23
$begingroup$
@user226375 your question is answered now,
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:42
$begingroup$
@user226375 your question is answered now,
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:42
$begingroup$
@andselisk you were correect .This was taken from Bruice's Organic chemistry.(missed reference ).How ever the answer is rewritten ti the question asked .The diagrams are mine , drawn on CHEMDRAW.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:44
$begingroup$
@andselisk you were correect .This was taken from Bruice's Organic chemistry.(missed reference ).How ever the answer is rewritten ti the question asked .The diagrams are mine , drawn on CHEMDRAW.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:44
2
2
$begingroup$
@andselisk I MISSED QUOTING REFERENECE IN HURRY TO ANSWER .MY APOLOGIES .THIS WAS NOT DONE ON PURPOUSE.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:52
$begingroup$
@andselisk I MISSED QUOTING REFERENECE IN HURRY TO ANSWER .MY APOLOGIES .THIS WAS NOT DONE ON PURPOUSE.
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:52
add a comment
|
Thanks for contributing an answer to Chemistry Stack Exchange!
- Please be sure to answer the question. Provide details and share your research!
But avoid …
- Asking for help, clarification, or responding to other answers.
- Making statements based on opinion; back them up with references or personal experience.
Use MathJax to format equations. MathJax reference.
To learn more, see our tips on writing great answers.
Sign up or log in
StackExchange.ready(function ()
StackExchange.helpers.onClickDraftSave('#login-link');
);
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
StackExchange.ready(
function ()
StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fchemistry.stackexchange.com%2fquestions%2f115942%2fhow-are-glycosidic-linkages-formed%23new-answer', 'question_page');
);
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function ()
StackExchange.helpers.onClickDraftSave('#login-link');
);
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function ()
StackExchange.helpers.onClickDraftSave('#login-link');
);
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function ()
StackExchange.helpers.onClickDraftSave('#login-link');
);
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
