How are glycosidic linkages formed?
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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
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$begingroup$
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
3458 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
3458 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
3458 bronze badges
asked May 26 at 5:52
user226375user226375
3458 bronze badges
asked May 26 at 5:52
user226375user226375
3458 bronze badges
asked May 26 at 5:52
user226375user226375
3458 bronze badges
asked May 26 at 5:52
user226375user226375
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3458 bronze badges
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1 Answer
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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
3,0171 gold badge5 silver badges25 bronze badges
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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.
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– andselisk♦
May 26 at 7:23
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@user226375 your question is answered now,
$endgroup$
– Chakravarthy Kalyan
May 26 at 8:42
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@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.
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– Chakravarthy Kalyan
May 26 at 8:44
2
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@andselisk I MISSED QUOTING REFERENECE IN HURRY TO ANSWER .MY APOLOGIES .THIS WAS NOT DONE ON PURPOUSE.
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– Chakravarthy Kalyan
May 26 at 8:52
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1 Answer
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1 Answer
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$begingroup$
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
3,0171 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
3,0171 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
3,0171 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
3,0171 gold badge5 silver badges25 bronze badges
edited May 26 at 8:47
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0171 gold badge5 silver badges25 bronze badges
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0171 gold badge5 silver badges25 bronze badges
answered May 26 at 7:12
Chakravarthy KalyanChakravarthy Kalyan
3,0171 gold badge5 silver badges25 bronze badges
3,0171 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
|
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