7.1! Monosaccharides and Disaccharides

Enantiomers are stereoisomers that are non-superimposable mirror images of each other.

Maltose is a disaccharide represented as Glc(α 1,4)Glc, formed from the hydrolysis of polysaccharides like glycogen or starch.

D-Fructose is a monosaccharide that exists as a mixture of pyranose and furanose forms in solution, with a higher tendency toward the pyranose form.

D-gluconic acid is an oxidative derivative of D-glucose where the aldehyde group is oxidized to a carboxylic acid.

A Fisher projection is a two-dimensional representation of a sugar molecule where vertical bonds represent groups going into the plane of the paper and horizontal bonds represent groups coming out of the plane.

Haworth projections are a way to represent cyclic forms of sugars, showing the molecule as cyclic and planar with substituents positioned above or below the ring.

The equatorial positions of bulky substituents in β-D-glucopyranose reduce steric hindrance, making this form more stable and common in nature.

β-D-glucopyranose is a cyclic form of D-glucose where all bulky substituents (OH and CH2OH) are in equatorial positions, contributing to its stability and prevalence in nature.

Diastereomers are stereoisomers that are non-superimposable and non-mirror images of each other.

Lactose is a reducing sugar because it contains a hemiacetal link that allows the anomeric carbon of glucose to revert to an open aldehyde form, making it susceptible to oxidation.

Glucose, an aldohexose, is a central sugar in metabolism.

Reducing sugars are sugars that can donate electrons to another chemical, typically characterized by the presence of a free aldehyde or ketone group.

Conformational isomers are isomers that interchange without breaking covalent bonds, such as chair and boat conformations of cyclic sugars.

An acetal is a compound formed from a hemiacetal when an additional alcohol reacts with it, resulting in the loss of water and the formation of two -OR groups.

The α and β designation indicates the orientation of the newly formed OH group at the glycosidic link; α means the O is pointing down, while β means the O is pointing up.

D-Ribose is a monosaccharide that predominantly exists in the furanose form in solution and is a crucial component of RNA.

The structure of lactose is represented as Gal(β1,4)Glc, indicating that it consists of galactose and glucose linked by a beta-1,4 bond.

Aldoses are sugars that contain an aldehyde group, while ketoses contain a ketone group.

a-D-Glucose is a common hexose sugar, an aldohexose that is a primary energy source for cells.

A carbohydrate is a general term that applies to simple sugars to complex sugar polymers like glycogen, starch, and cellulose.

D-glucose is a simple sugar (monosaccharide) that is an important energy source in living organisms and is a primary product of photosynthesis.

A hemiacetal is a compound formed when an alcohol reacts with an aldehyde, resulting in a carbon atom bonded to both an -OH group and an -OR group.

D-glucaric acid is a sugar acid derived from glucose, where both the C1 and C6 positions are oxidized to carboxylic acids.

Non-reducing sugars are sugars that cannot open to form an aldehyde or ketone, such as sucrose, which is a disaccharide made of glucose and fructose.

Phosphorylated forms of monosaccharides are derivatives formed when phosphates are transferred from ATP to create phosphoester derivatives.

a-D-Mannose is a type of aldohexose sugar that is an epimer of a-D-Glucose and plays a role in glycoprotein synthesis.

Configurational isomers are isomers that can only be interconverted by breaking covalent bonds.

Alpha-gal syndrome is a disease caused by a tick bite that leads to an immune response against the disaccharide galactose-α-1,3-galactose, resulting in allergic reactions to red meat and other products containing this disaccharide.

Anomers are a specific type of diastereomer that differ only at the hemiacetal or acetal carbon.

Sucrose is a non-reducing sugar because it is formed by the acetal linkage of glucose and fructose through the anomeric OH of fructose, preventing it from existing in equilibrium with its straight-chain form.

The Chair conformation is a stable three-dimensional structure of cyclic sugars that minimizes steric strain.

D-glucuronic acid is a derivative of glucose where the C6 hydroxymethyl group is oxidized to a carboxylic acid.

The anomers of cyclic sugars are classified as α anomer, where the hydroxyl group points below the ring, and β anomer, where it points above the ring.

D-Glucose is a monosaccharide that primarily exists in the pyranose form in solution and is a key energy source for cells.

Oxidizing agents are mild and react with aldehydes in reducing sugars, facilitating the reduction of a basic blue solution of CuSO4 to a brick-red precipitate of Cu+.

Hemiacetal links in sugars indicate that the sugar can exist in a form that allows it to revert to an aldehyde, thus classifying it as a reducing sugar.

Furanose refers to a 5-membered ring structure, while pyranose refers to a 6-membered ring structure formed by the cyclization of sugars.

Neu5Gc can be incorporated into human membrane glycans when non-vegan humans consume animal products, potentially increasing susceptibility to certain bacterial toxins.

Amine derivatives of monosaccharides include compounds such as glucosamine or galactosamine.

a-D-glucopyranose is a cyclic form of glucose, a monosaccharide that is commonly found in various carbohydrates, including starch and glycogen.

A glycan is a general term for molecules containing simple sugars and sugar derivatives linked in a polymer, either as standalone molecules or attached to other molecules like proteins.

The Fischer projection is a two-dimensional representation of a molecule that shows the configuration of its chiral centers, typically used for sugars.

An acetal is a compound formed from a hemiacetal by the addition of another alcohol, resulting in a carbon atom bonded to two -OR groups.

a-D-Galactose is an aldohexose sugar that is an epimer of a-D-Glucose and is important in the formation of lactose.

Lactose, also known as milk sugar, is a disaccharide structured as Gal(β 1,4)Glc, consisting of galactose and glucose linked by a β-1,4 glycosidic bond.

Glucose is a simple sugar (monosaccharide) with the formula C6H12O6, which is a primary source of energy for cells.

The equilibrium between straight and cyclic forms of monosaccharides is important for their reactivity and stability in solution, influencing their biological functions.

N-acetylmuramic acid is a component of bacterial cell walls that consists of N-acetylglucosamine linked to lactate.

Sialic acids are a family of nine-carbon sugars that are typically found on the surface of cells and play a role in cell recognition and signaling.

D-glucose is a simple sugar (monosaccharide) that serves as an important energy source in living organisms and is a primary product of photosynthesis.

Reducing sugars are disaccharides or other sugars that can act as reducing agents because they have a potentially open aldehyde at C1 or an α-hydroxymethyl ketone group that can isomerize to an aldehyde under basic conditions.

b-D-galactopyranose is a cyclic form of galactose, a monosaccharide that is part of lactose, characterized by its specific configuration at the anomeric carbon.

Alpha and beta anomers refer to the two different configurations of a sugar at the anomeric carbon; in alpha, the hydroxyl group is down, and in beta, it is up.

The most common monosaccharides are aldo- and keto-trioses, tetroses, pentoses, and hexoses.

Diastereomers are stereoisomers that are not mirror images of each other.

A hemiacetal is a compound formed when an alcohol reacts with an aldehyde, resulting in a carbon atom bonded to both an -OH group and an -OR group.

Acetylated amine derivatives are compounds like N-Acetyl-GlcNAc (GlcNAc) or GalNAc, formed by the acetylation of amine derivatives.

A glycosidic link is the acetal bond that forms between two monosaccharides, typically involving the anomeric carbon of one of the sugars.

Wedge/dash projections are a method of representing three-dimensional structures of molecules, indicating the orientation of bonds in space with wedges for bonds coming out of the plane and dashes for bonds going behind the plane.

The cyclic forms of D-Glucose include alpha-D-glucopyranose and beta-D-glucopyranose, which differ in the orientation of the hydroxyl group on the anomeric carbon.

A sugar usually refers to low molecular weight carbohydrates like glucose, lactose, and sucrose, but can also refer broadly to any carbohydrate.

Lactose is a disaccharide sugar composed of one molecule of galactose and one molecule of glucose linked by a β(1→4) glycosidic bond.

Individuals with Alpha-gal syndrome may experience allergic reactions ranging from mild rashes to severe anaphylactic responses after consuming red meat due to their immune response to the disaccharide galactose-α-1,3-galactose.

Reducing sugars are sugars that can open to form an aldehyde or a ketone, allowing them to reduce other compounds, such as in the case of glucose and galactose.

Oxidized forms of monosaccharides are derivatives where the aldehyde and/or alcohol functional groups are oxidized to carboxylic acids.

Haworth projections are a way to represent the cyclic forms of sugars, showing the orientation of substituents around the ring.

A wedge and dash drawing is a three-dimensional representation of a molecule that shows the spatial orientation of atoms, with wedges indicating bonds coming out of the plane and dashes indicating bonds going into the plane.

Enantiomers are stereoisomers that are mirror images of each other and are nonsuperimposable.

N-acetylneuraminic acid, also known as Neu5Ac, is a sialic acid that results from the cyclization of a condensation product of N-acetylmannosamine and pyruvate.

Sugars can be defined as polyhydroxy-aldehydes or ketones, with the simplest sugars containing at least three carbon atoms.

The D and L designations refer to the configuration of the chiral center most distant from the aldehyde or ketone group, with D sugars being related to D-glyceraldehyde.

In chair conformations, equatorial positions are favored for bulky groups to minimize steric hindrance, while axial positions can lead to steric clashes.

Epimers are diastereomers that differ at one stereocenter other than at the acetal or hemiacetal carbon.

Lactone forms are intramolecular esters in which an OH group attacks a carbonyl carbon that was previously oxidized to a carboxylic acid.