Cellulose: Difference between revisions
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==Structure== | ==Structure== | ||
<StructureSection load='' size=' | <StructureSection load='' size='489' side='right' scene='82/824000/Cellobiose/4'> | ||
Glucose, the building block of cellulose and starch, can form six-membered rings with two distinct stereoisomers called the alpha and beta anomer. The only difference between alpha and beta glucose is at carbon C1. The [[disaccharides|disaccharide]] cellobiose (reload <scene name='82/824000/Cellobiose/4'>initial scene</scene>) is a breakdown product of cellulose which shows the beta 1,4 linkage between two glucose molecules also present in cellulose. "beta 1,4" refers to a glycosidic link between the anomeric carbon (<jmol><jmolLink><script> select 823.C1; selectionHalos ON; delay 0.5;selectionHalos OFF;</script><text>☼</text></jmolLink> </jmol>) in beta configuration of one glucose molecule with carbon 4 (<jmol><jmolLink><script> select 823.C4'; selectionHalos ON; delay 0.5;selectionHalos OFF;</script><text>☼</text></jmolLink> </jmol>) of the other glucose molecule. | Glucose, the building block of cellulose and starch, can form six-membered rings with two distinct stereoisomers called the alpha and beta anomer. The only difference between alpha and beta glucose is at carbon C1. The [[disaccharides|disaccharide]] cellobiose (reload <scene name='82/824000/Cellobiose/4'>initial scene</scene>) is a breakdown product of cellulose which shows the beta 1,4 linkage between two glucose molecules also present in cellulose. "beta 1,4" refers to a glycosidic link between the anomeric carbon (<jmol><jmolLink><script> spin off; select 823.C1; selectionHalos ON; delay 0.5;selectionHalos OFF;</script><text>☼</text></jmolLink> </jmol>) in beta configuration of one glucose molecule with carbon 4 (<jmol><jmolLink><script> select 823.C4'; selectionHalos ON; delay 0.5;selectionHalos OFF;</script><text>☼</text></jmolLink> </jmol>) of the other glucose molecule. In contrast, starches (specifically the linear form [[amylose]]) can be broken down to [[disaccharides|maltose]], a stereoisomer of cellobiose showing an alpha 1,4 linkage. Thus, it is the type of glycosidic linkage that distinguishes cellulose from starches at the molecular level. | ||
Longer chains of beta 1,4 linked glucoses are found in cellulose. When cellulose is synthesized, these chains are made individually (cellulose chain during <scene name='82/824000/Cellulose/2'>biosynthesis</scene>). Again, the linkages are all of the beta 1,4 type (<jmol><jmolLink><script> select *.C1; selectionHalos ON; delay 0.5;selectionHalos OFF;</script><text>☼</text></jmolLink> </jmol>). In this structure, monomers are added to polymer chain inside the cell and secreted through the membrane, surrounded by the <scene name='82/824000/Cellulose/4'>enzyme</scene> throughout. | Longer chains of beta 1,4 linked glucoses are found in cellulose. When cellulose is synthesized, these chains are made individually (cellulose chain during <scene name='82/824000/Cellulose/2'>biosynthesis</scene>)<ref>DOI:10.1098/rsta.2017.0048</ref>. Again, the linkages are all of the beta 1,4 type (<jmol><jmolLink><script> select BGC and *.C1; selectionHalos ON; delay 0.5;selectionHalos OFF;</script><text>☼</text></jmolLink> </jmol>). In this structure, monomers are added to polymer chain inside the cell and secreted through the membrane, surrounded by the <scene name='82/824000/Cellulose/4'>enzyme</scene> throughout. | ||
Once secreted, individual cellulose chains | Once secreted, individual cellulose chains self-assemble to from semi-crystalline cellulose microfibrils. There are multiple forms of cellulose (I alpha and beta, II, III) which differ in the orientation and the detailed interactions between linear polymers. A model of a <scene name='82/824000/Microfibril/4'>cellulose type I beta micro-fibril</scene> shows a tightly packed structure. The model was made using cellulose builder (http://cces-sw.iqm.unicamp.br/cces/admin/cellulose, <ref>DOI:10.1002/jcc.22959</ref>) and is based on a fiber-diffraction study by Nishiyama et al <ref>DOI:10.1021/ja0257319</ref>. The <scene name='82/824000/Microfibril1d/1'>individual chains</scene> of cellulose form <scene name='82/824000/Microfibril2d/1'>layers</scene>, and multiple layers stack to form a <scene name='82/824000/Microfibril3d/1'>3D structure</scene> without any gaps. While interactions within layers are dominated by hydrogen bonding, <scene name='82/824000/Hydrophobic/1'>interactions between layers</scene> are hydrophobic<ref>DOI:10.1007/s10570-021-04325-4</ref>. You can use the buttons below to explore the 1D, 2D and 3D assembly of the microfibril model. | ||
Repeating unit | |||
Style <jmol> | |||
<jmolRadioGroup> | |||
<item> | |||
<script>select (4-5 and chain=M);spacefill only</script> | |||
<text>spacefill</text> | |||
</item> | |||
<item> | |||
<script>select (4-5 and chain=M);set bondmode OR; wireframe only</script> | |||
<text>bonds</text> | |||
</item> | |||
<item> | |||
<script>select 4-5 and chain=M;set bondmode OR; wireframe only; wireframe 0.2; spacefill 0.5</script> | |||
<text>ball-and-stick</text> | |||
<checked>true</checked> | |||
</item> | |||
</jmolRadioGroup> | |||
</jmol> | |||
Color <jmol> | |||
<jmolRadioGroup> | |||
<item> | |||
<script>select (4-5 and chain=M); color chain</script> | |||
<text>by chain</text> | |||
</item> | |||
<item> | |||
<script>select (4-5 and chain=M); color cpk</script> | |||
<text>by atomtype</text> | |||
</item> | |||
<item> | |||
<script>select (4-5 and chain=M); color black</script> | |||
<text>black</text> | |||
<checked>true</checked> | |||
</item> | |||
</jmolRadioGroup> | |||
</jmol> | |||
Rest of microfibril | |||
Show <jmol> | |||
<jmolRadioGroup> | |||
<item> | |||
<script>display chain=M and 4-5</script> | |||
<text>none</text> | |||
</item> | |||
<item> | |||
<script>display chain=M</script> | |||
<text>1D</text> | |||
</item> | |||
<item> | |||
<script>display chain=B or chain=G or chain=M or chain=R</script> | |||
<text>2D</text> | |||
</item> | |||
<item> | |||
<script>display all</script> | |||
<text>3D</text> | |||
<checked>true</checked> | |||
</item> | |||
</jmolRadioGroup> | |||
</jmol> | |||
Style <jmol> | |||
<jmolRadioGroup> | |||
<item> | |||
<script>select not (4-5 and chain=M);spacefill only</script> | |||
<text>spacefill</text> | |||
</item> | |||
<item> | |||
<script>select not (4-5 and chain=M);wireframe only</script> | |||
<text>bonds</text> | |||
</item> | |||
<item> | |||
<script>select not (4-5 and chain=M);wireframe only; wireframe 0.2; spacefill 20%</script> | |||
<text>ball-and-stick</text> | |||
<checked>true</checked> | |||
</item> | |||
</jmolRadioGroup> | |||
</jmol> | |||
Color <jmol> | |||
<jmolRadioGroup> | |||
<item> | |||
<script>select not (4-5 and chain=M); color chain</script> | |||
<text>by chain</text> | |||
</item> | |||
<item> | |||
<script>select not (4-5 and chain=M); color cpk</script> | |||
<text>by atomtype</text> | |||
</item> | |||
<item> | |||
<script>select not (4-5 and chain=M); color black</script> | |||
<text>black</text> | |||
<checked>true</checked> | |||
</item> | |||
</jmolRadioGroup> | |||
</jmol> | |||
<jmol> | |||
<jmolCheckbox> | |||
<scriptWhenUnChecked>hbond off | |||
</scriptWhenUnChecked> | |||
<scriptWhenchecked>select all; hbond on | |||
</scriptWhenchecked> | |||
<checked>false</checked> | |||
<text>hydrogen bonds</text> | |||
</jmolCheckbox> | |||
</jmol> | |||
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==See also== | ==See also== | ||
Lecture slides by Eero Kontturi, Aalto University, Espoo, Finland: https://mycourses.aalto.fi/pluginfile.php/148341/mod_folder/content/0/Lecture%202%20-%20Cellulose%20structure.pdf?forcedownload=1 | |||
== References == | == References == | ||
<references/> | <references/> | ||
Latest revision as of 20:25, 6 July 2023
Cellulose is the most abundant biopolymer on earth. It occurs in plant cell walls and in bacteria. Common materials containing high amounts of cellulose are wood, paper, and cotton. Cellulose is a water-insoluble polysaccharide that humans can not digest. It is a linear polymer of beta-1,4 linked glucose building blocks, with chains arranged in microfibrils held together by hydrogen bonds and hydrophobic interactions. Cellulose is related to but distinct from starch, a water-soluble carbohydrate containing alpha-1,4 linked glucose building blocks that is digestible by humans.
StructureStructure
Glucose, the building block of cellulose and starch, can form six-membered rings with two distinct stereoisomers called the alpha and beta anomer. The only difference between alpha and beta glucose is at carbon C1. The disaccharide cellobiose (reload ) is a breakdown product of cellulose which shows the beta 1,4 linkage between two glucose molecules also present in cellulose. "beta 1,4" refers to a glycosidic link between the anomeric carbon () in beta configuration of one glucose molecule with carbon 4 () of the other glucose molecule. In contrast, starches (specifically the linear form amylose) can be broken down to maltose, a stereoisomer of cellobiose showing an alpha 1,4 linkage. Thus, it is the type of glycosidic linkage that distinguishes cellulose from starches at the molecular level. Longer chains of beta 1,4 linked glucoses are found in cellulose. When cellulose is synthesized, these chains are made individually (cellulose chain during )[1]. Again, the linkages are all of the beta 1,4 type (). In this structure, monomers are added to polymer chain inside the cell and secreted through the membrane, surrounded by the throughout. Once secreted, individual cellulose chains self-assemble to from semi-crystalline cellulose microfibrils. There are multiple forms of cellulose (I alpha and beta, II, III) which differ in the orientation and the detailed interactions between linear polymers. A model of a shows a tightly packed structure. The model was made using cellulose builder (http://cces-sw.iqm.unicamp.br/cces/admin/cellulose, [2]) and is based on a fiber-diffraction study by Nishiyama et al [3]. The of cellulose form , and multiple layers stack to form a without any gaps. While interactions within layers are dominated by hydrogen bonding, are hydrophobic[4]. You can use the buttons below to explore the 1D, 2D and 3D assembly of the microfibril model. Repeating unit Style Color
Rest of microfibril Show Style Color
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See alsoSee also
Lecture slides by Eero Kontturi, Aalto University, Espoo, Finland: https://mycourses.aalto.fi/pluginfile.php/148341/mod_folder/content/0/Lecture%202%20-%20Cellulose%20structure.pdf?forcedownload=1
ReferencesReferences
- ↑ Turner S, Kumar M. Cellulose synthase complex organization and cellulose microfibril structure. Philos Trans A Math Phys Eng Sci. 2018 Feb 13;376(2112):20170048. doi: , 10.1098/rsta.2017.0048. PMID:29277745 doi:http://dx.doi.org/10.1098/rsta.2017.0048
- ↑ Gomes TC, Skaf MS. Cellulose-builder: a toolkit for building crystalline structures of cellulose. J Comput Chem. 2012 May 30;33(14):1338-46. doi: 10.1002/jcc.22959. Epub 2012 Mar , 15. PMID:22419406 doi:http://dx.doi.org/10.1002/jcc.22959
- ↑ Nishiyama Y, Langan P, Chanzy H. Crystal structure and hydrogen-bonding system in cellulose Ibeta from synchrotron X-ray and neutron fiber diffraction. J Am Chem Soc. 2002 Aug 7;124(31):9074-82. doi: 10.1021/ja0257319. PMID:12149011 doi:http://dx.doi.org/10.1021/ja0257319
- ↑ DOI:10.1007/s10570-021-04325-4