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Pyranose

About: Pyranose is a research topic. Over the lifetime, 1619 publications have been published within this topic receiving 35348 citations. The topic is also known as: pyranoses & hexopyranose.


Papers
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Journal ArticleDOI
01 Jun 2016-Proteins
TL;DR: Spirochaeta thermophila secretes seven glycoside hydrolases for plant biomass degradation that carry a carbohydrate‐binding module 64 (CBM64) appended at the C‐terminus that achieves association with the hydrophobic face of β‐linked pyranose chains via a unique coplanar arrangement of four exposed tryptophan side chains.
Abstract: Spirochaeta thermophila secretes seven glycoside hydrolases for plant biomass degradation that carry a carbohydrate-binding module 64 (CBM64) appended at the C-terminus. CBM64 adsorbs to various β1-4-linked pyranose substrates and shows high affinity for cellulose. We present the first crystal structure of a CBM64 at 1.2 A resolution, which reveals a jelly-roll-like fold corresponding to a surface-binding type A CBM. Modeling of its interaction with cellulose indicates that CBM64 achieves association with the hydrophobic face of β-linked pyranose chains via a unique coplanar arrangement of four exposed tryptophan side chains. Proteins 2016; 84:855-858. © 2016 Wiley Periodicals, Inc.

15 citations

Journal ArticleDOI
TL;DR: The results of simulations relying on the new set of parameters indicate that the conformation of glycosidic linkage is nearly unaffected by the chemical state of the carboxyl group, in contrary to the ring conformational equilibria.
Abstract: An extension of the GROMOS 56a6CARBO/CARBO_R force field for hexopyranose-based carbohydrates is presented. The additional parameters describe the conformational properties of uronate residues. The three distinct chemical states of the carboxyl group are considered: deprotonated (negatively charged), protonated (neutral), and esterified (neutral). The parametrization procedure was based on quantum-chemical calculations, and the resulting parameters were tested in the context of (i) flexibility of the pyranose rings under different pH conditions, (ii) conformation of the glycosidic linkage of the (1 → 4)-type for uronates with different chemical states of carboxyl moieties, (iii) conformation of the exocyclic (i.e., carboxylate and lactol) moieties, and (iv) structure of the Ca2+-linked chain–chain complexes of uronates. The presently proposed parameters in combination with the 56a6CARBO/CARBO_R set can be used to describe the naturally occurring polyuronates, composed either of homogeneous (e.g., glucuron...

15 citations

Journal ArticleDOI
TL;DR: The production and purification of indochrome, the soluble pigment from Arthrobacter polychromogenes, is described and all d-ribopyranosyl residues were found to be in the C1(D) conformation.
Abstract: The production and purification of indochrome, the soluble pigment from Arthrobacter polychromogenes, is described. Four isomeric 3-hydroxy-6-d-ribosyl-2-aza-benzoquinone-(1,4)-4-[2,6-dihydroxy-5-d-ribosyl-pyridyl-(3)-imides] have been isolated from the natural product as the main components. In indochrome A two β-d-ribopyranosyl residues, in indochrome B II two β-d-ribofuranosyl residues, are bound to the aglycone. The pigment fractions B I and B III contain differently configurated d-ribosyl residues, which for B I were found to be the α- and β-configurations of the pyranose form. Nitric acid degradation of the pigment and condensation with phenylhydrazine yields mainly 3-β-d-ribopyranosyl-5-benzeneazo-2,6-dihydroxy-pyridine. All d-ribopyranosyl residues were found to be in the C1(D) conformation. d-Ribose was liberated from the aglycones by ozonolysis.

15 citations

Journal ArticleDOI
TL;DR: Carbohydrate exo 1,2-orthoesters are obtained in good yields by treating furanose and pyranose hemiacetals first with 1.1 eq. 1-chloro-2,N,N-trimethyl-propenylamine and then with the appropriate alcohols in the presence of NEt3.

14 citations

Journal ArticleDOI
TL;DR: The formation of C-C bonds at the anomeric center of carbohydrates has become an important area in organic synthesis as mentioned in this paper, and the Lewis acid catalyzed addition of carbon nucleophiles to electrophilic sugar derivatives is the most popular method generally affording α-C-glycosides in the pyranose series.

14 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202317
202228
202118
202027
201926
201819