organic chemistry Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, and reactions of organic compounds and organic materials, i.e., matter in its various forms that contain carbon atoms.Clayden, ...

and

biochemistry Biochemistry or biological chemistry is the study of chemical processes within and relating to living organisms. A sub-discipline of both chemistry and biology, biochemistry may be divided into three fields: structural biology, enzymology and ...

, a side chain is a

chemical group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

that is attached to a core part of the molecule called the "main chain" or

backbone The backbone is the vertebral column of a vertebrate. Arts, entertainment, and media Film * ''Backbone'' (1923 film), a 1923 lost silent film starring Alfred Lunt * ''Backbone'' (1975 film), a 1975 Yugoslavian drama directed by Vlatko Gilić ...

. The side chain is a hydrocarbon branching element of a molecule that is attached to a larger hydrocarbon backbone. It is one factor in determining a molecule's properties and reactivity. A side chain is also known as a pendant chain, but a pendant group (side group) has a different definition.

Conventions

The placeholder R is often used as a generic placeholder for

alkyl In organic chemistry, an alkyl group is an alkane missing one hydrogen. The term ''alkyl'' is intentionally unspecific to include many possible substitutions. An acyclic alkyl has the general formula of . A cycloalkyl is derived from a cycloa ...

(saturated hydrocarbon) group side chains in chemical structure diagrams. To indicate other non-carbon groups in structure diagrams, X, Y, or Z are often used.

History

The ''R'' symbol was introduced by 19th-century French

chemist A chemist (from Greek ''chēm(ía)'' alchemy; replacing ''chymist'' from Medieval Latin ''alchemist'') is a scientist trained in the study of chemistry. Chemists study the composition of matter and its properties. Chemists carefully describe t ...

Charles Frédéric Gerhardt, who advocated its adoption on the grounds that it would be widely recognizable and intelligible given its correspondence in multiple

European languages Most languages of Europe belong to the Indo-European language family. Out of a total European population of 744 million as of 2018, some 94% are native speakers of an Indo-European language. Within Indo-European, the three largest phyla are Ro ...

to the initial letter of "root" or "residue": French ''racine'' ("root") and ''résidu'' ("residue"), these terms' respective English translations along with '' radical'' (itself derived from Latin ''radix'' below), Latin ''radix'' ("root") and ''residuum'' ("residue"), and German ''Rest'' ("remnant" and, in the context of chemistry, both "residue" and "radical").

Usage

Organic chemistry

polymer science Polymer science or macromolecular science is a subfield of materials science concerned with polymers, primarily synthetic polymers such as plastics and elastomers. The field of polymer science includes researchers in multiple disciplines includ ...

, the side chain of an oligomeric or

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

ic offshoot extends from the

backbone chain In polymer science, the polymer chain or simply backbone of a polymer is the main chain of a polymer. Polymers are often classified according to the elements in the main chains. The character of the backbone, i.e. its flexibility, determines the ...

of a polymer. Side chains have noteworthy influence on a polymer's properties, mainly its crystallinity and

density Density (volumetric mass density or specific mass) is the substance's mass per unit of volume. The symbol most often used for density is ''ρ'' (the lower case Greek letter rho), although the Latin letter ''D'' can also be used. Mathematical ...

. An

oligomeric In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...

branch may be termed a short-chain branch, and a

polymeric A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic an ...

branch may be termed a long-chain branch.

Side group In IUPAC nomenclature of chemistry, a pendant group (sometimes spelled pendent) or side group is a group of atoms attached to a backbone chain of a long molecule, usually a polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") ...

s are different from side chains; they are neither oligomeric nor polymeric.

Biochemistry

protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, res ...

s, which are composed of

amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although hundreds of amino acids exist in nature, by far the most important are the alpha-amino acids, which comprise proteins. Only 22 alpha a ...

residues, the side chains are attached to the

alpha-carbon In the nomenclature of organic chemistry, a locant is a term to indicate the position of a functional group or substituent within a molecule. Numeric locants The International Union of Pure and Applied Chemistry (IUPAC) recommends the use of n ...

atoms of the

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a compound with the general formula , where R, R', and R″ represent organic groups or hydrogen atoms. The amide group is called a peptide bond when it i ...

backbone. The side chain connected to the alpha-carbon is specific for each amino acid and is responsible for determining

charge Charge or charged may refer to: Arts, entertainment, and media Films * '' Charge, Zero Emissions/Maximum Speed'', a 2011 documentary Music * ''Charge'' (David Ford album) * ''Charge'' (Machel Montano album) * ''Charge!!'', an album by The Aqu ...

and polarity of the amino acid. The amino acid side chains are also responsible for many of the interactions that lead to proper

protein folding Protein folding is the physical process by which a protein chain is translated to its native three-dimensional structure, typically a "folded" conformation by which the protein becomes biologically functional. Via an expeditious and reproduc ...

and function. Amino acids with similar polarity are usually attracted to each other, while nonpolar and polar side chains usually repel each other. Nonpolar/polar interactions can still play an important part in stabilizing the secondary structure due to the relatively large amount of them occurring throughout the protein. Spatial positions of side-chain atoms can be predicted based on protein backbone geometry using computational tools for side-chain reconstruction. AAs_table

References