Cellulose

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 ). 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 . are completely surrounded. 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 tightly packed structure. The model was made using cellulose builder (http://cces-sw.iqm.unicamp.br/cces/admin/cellulose, ^[1]) and is based on a fiber-diffraction study by Nishiyama et al ^[2]. The of cellulose form held together by , and to form a 3D structure without any gaps. While interactions within layers are dominated by hydrogen bonding, are hydrophobic.

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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

1. ↑ 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
2. ↑ 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