Alpha and beta carbon

The alpha carbon (Cα) in organic molecules refers to the first carbon atom that
attaches to a functional group, such as a carbonyl. The second carbon atom is called
the beta carbon (Cβ),[1] and the system continues naming in alphabetical order with
Greek letters.

The nomenclature can also be applied to the hydrogen atoms attached to the carbon
atoms. A hydrogen atom attached to an alpha carbon atom is called an alpha-
hydrogen atom, a hydrogen atom on the beta-carbon atom is a beta hydrogen atom,
and so on. Alpha and beta carbons in the
skeletal formula of benzylacetone.
This naming standard may not be in compliance with IUPAC nomenclature, which The carbonyl has two β-hydrogens
and five γ-hydrogens
encourages that carbons be identified by number, not by Greek letter, but it
nonetheless remains very popular, in particular because it is useful in identifying the
relative location of carbon atoms to other functional groups.

Organic molecules with more than one functional group can be a source of confusion. Generally the functional group responsible for
the name or type of the molecule is the 'reference' group for purposes of carbon-atom naming. For example, the molecules
nitrostyrene and phenethylamine are very similar; the former can even be reduced into the latter. However, nitrostyrene's α-carbon
atom is adjacent to the phenyl group; in phenethylamine this same carbon atom is the β-carbon atom, as phenethylamine (being an
[1]
amine rather than a styrene) counts its atoms from the opposite "end" of the molecule.

Contents
Examples
Proteins and amino acids
Enols and enolates
References

Examples

Proteins and amino acids

Alpha-carbon (α-carbon) is also a term that applies to proteins and amino
acids. It is the backbone carbon before the carbonyl carbon. Therefore, reading
along the backbone of a typical protein would give a sequence of –[N—Cα—
carbonyl C]n– etc. (when reading in the N to C direction). The α-carbon is
where the different substituents attach to each different amino acid. That is, the
Skeletal formula of butyric acid with the
groups hanging off the chain at the α-carbon are what give amino acids their alpha, beta, and gamma carbons marked
diversity. These groups give the α-carbon its stereogenic properties for every
amino acid except for glycine. Therefore, the α-carbon is a stereocenter for
every amino acid except glycine. Glycine also does not have a β-carbon, while every other amino acid does.
The α-carbon of an amino acid is significant in protein folding. When describing a protein, which is a chain of amino acids, one often
approximates the location of each amino acid as the location of its α-carbon. In general, α-carbons of adjacent amino acids in a
protein are about 3.8 ångströms (380 picometers) apart.

Enols and enolates

The α-carbon is important for enol- and enolate-based carbonyl chemistry as well. Chemical transformations affected by the
conversion to either an enolate or an enol, in general, lead to the α-carbon acting as a nucleophile, becoming, for example, alkylated
in the presence of primary haloalkane. An exception is in reaction with silyl -chlorides, -bromides, and -iodides, where the oxygen
acts as the nucleophile to producesilyl enol ether.

References
1. "Nomenclature" (http://www.cognitiveliberty.org/shulgin/adsarchive/nomenclature.htm). Ask Dr. Shulgin Online.
Retrieved August 5, 2010.

1. ^ Hackh's Chemical Dictionary, 1969, page 30.

2. ^ Hackh's Chemical Dictionary, 1969, page 95.

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