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In
chemistry Chemistry is the scientific study of the properties and behavior of matter. It is a physical science within the natural sciences that studies the chemical elements that make up matter and chemical compound, compounds made of atoms, molecules a ...
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, a ...
, an oligomer () is a
molecule A molecule is a group of two or more atoms that are held together by Force, attractive forces known as chemical bonds; depending on context, the term may or may not include ions that satisfy this criterion. In quantum physics, organic chemi ...
that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules,
monomers A monomer ( ; ''wikt:mono-, mono-'', "one" + ''wikt:-mer, -mer'', "part") is a molecule that can chemical reaction, react together with other monomer molecules to form a larger polymer chain or two- or three-dimensional network in a process called ...
.Quote: ''Oligomer molecule: A molecule of intermediate relative molecular mass, the structure of which essentially comprises a small plurality of units derived, actually or conceptually, from molecules of lower relative molecular mass.'' The name is composed of
Greek Greek may refer to: Anything of, from, or related to Greece, a country in Southern Europe: *Greeks, an ethnic group *Greek language, a branch of the Indo-European language family **Proto-Greek language, the assumed last common ancestor of all kno ...
elements '' oligo-'', "a few" and '' -mer'', "parts". An
adjective An adjective (abbreviations, abbreviated ) is a word that describes or defines a noun or noun phrase. Its semantic role is to change information given by the noun. Traditionally, adjectives are considered one of the main part of speech, parts of ...
form is ''oligomeric''. The oligomer concept is contrasted to that of a
polymer A polymer () is a chemical substance, substance or material that consists of very large molecules, or macromolecules, that are constituted by many repeat unit, repeating subunits derived from one or more species of monomers. Due to their br ...
, which is usually understood to have a large number of units, possibly thousands or millions. However, there is no sharp distinction between these two concepts. One proposed criterion is whether the molecule's properties vary significantly with the removal of one or a few of the units. An oligomer with a specific number of units is referred to by the Greek prefix denoting that number, with the ending ''-mer'': thus dimer, trimer,
tetramer A tetramer () (''tetra-'', "four" + '' -mer'', "parts") is an oligomer formed from four monomers or subunits. The associated property is called ''tetramery''. An example from inorganic chemistry is titanium methoxide with the empirical formula ...
,
pentamer A pentamer is an entity composed of five subunits. In chemistry, it applies to molecules made of five monomers. In biochemistry, it applies to macromolecules, particularly pentameric proteins, made of five protein sub-units. In microbiology, a ...
, and
hexamer 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, monomer, monomers.Quote: ''Oligomer molecule: A molecule of intermediate ...
refer to molecules with two, three, four, five, and six units, respectively. The units of an oligomer may be arranged in a linear chain (as in melam, a dimer of
melamine Melamine is an organic compound with the formula C3H6N6. This white solid is a trimer (chemistry), trimer of cyanamide, with a 1,3,5-Triazine, 1,3,5-triazine skeleton. Like cyanamide, it contains 66% nitrogen by mass, and its derivatives ha ...
); a closed ring (as in 1,3,5-trioxane, a cyclic trimer of
formaldehyde Formaldehyde ( , ) (systematic name methanal) is an organic compound with the chemical formula and structure , more precisely . The compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde. It is stored as ...
); or a more complex structure (as in
tellurium tetrabromide Tellurium tetrabromide ( Te Br4) is an inorganic chemical compound. It has a similar tetrameric structure to TeCl4.''Inorganic Chemistry'',Egon Wiberg, Arnold Frederick Holleman Elsevier 2001 It can be made by reacting bromine and tellurium. In ...
, a tetramer of with a
cube A cube or regular hexahedron is a three-dimensional space, three-dimensional solid object in geometry, which is bounded by six congruent square (geometry), square faces, a type of polyhedron. It has twelve congruent edges and eight vertices. It i ...
-like core). If the units are identical, one has a ''homo-oligomer''; otherwise one may use ''hetero-oligomer''. An example of a homo-oligomeric protein is
collagen Collagen () is the main structural protein in the extracellular matrix of the connective tissues of many animals. It is the most abundant protein in mammals, making up 25% to 35% of protein content. Amino acids are bound together to form a trip ...
, which is composed of three identical protein chains. Some biologically important oligomers are macromolecules like
protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residue (biochemistry), residues. Proteins perform a vast array of functions within organisms, including Enzyme catalysis, catalysing metab ...
s or
nucleic acids Nucleic acids are large biomolecules that are crucial in all cells and viruses. They are composed of nucleotides, which are the monomer components: a 5-carbon sugar, a phosphate group and a nitrogenous base. The two main classes of nucleic a ...
; for instance,
hemoglobin Hemoglobin (haemoglobin, Hb or Hgb) is a protein containing iron that facilitates the transportation of oxygen in red blood cells. Almost all vertebrates contain hemoglobin, with the sole exception of the fish family Channichthyidae. Hemoglobin ...
is a protein tetramer. An oligomer of
amino acid Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the 22 α-amino acids incorporated into proteins. Only these 22 a ...
s is called an oligopeptide or just a
peptide Peptides are short chains of amino acids linked by peptide bonds. A polypeptide is a longer, continuous, unbranched peptide chain. Polypeptides that have a molecular mass of 10,000 Da or more are called proteins. Chains of fewer than twenty am ...
. An
oligosaccharide An oligosaccharide (; ) is a carbohydrate, saccharide polymer containing a small number (typically three to ten) of monosaccharides (simple sugars). Oligosaccharides can have many functions including Cell–cell recognition, cell recognition and ce ...
is an oligomer of
monosaccharide Monosaccharides (from Greek '' monos'': single, '' sacchar'': sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. Chemically, monosaccharides are polyhy ...
s (simple sugars). An
oligonucleotide Oligonucleotides are short DNA or RNA molecules, oligomers, that have a wide range of applications in genetic testing, Recombinant DNA, research, and Forensic DNA, forensics. Commonly made in the laboratory by Oligonucleotide synthesis, solid-phase ...
is a short single-stranded fragment of
nucleic acid Nucleic acids are large biomolecules that are crucial in all cells and viruses. They are composed of nucleotides, which are the monomer components: a pentose, 5-carbon sugar, a phosphate group and a nitrogenous base. The two main classes of nuclei ...
such as
DNA Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...
or
RNA Ribonucleic acid (RNA) is a polymeric molecule that is essential for most biological functions, either by performing the function itself (non-coding RNA) or by forming a template for the production of proteins (messenger RNA). RNA and deoxyrib ...
, or similar fragments of analogs of nucleic acids such as
peptide nucleic acid Peptide nucleic acid (PNA) is an artificially synthesized polymer similar to DNA or RNA. Synthetic peptide nucleic acid oligomers have been used in recent years in molecular biology procedures, diagnostic assays, and antisense therapies. Due to ...
or
Morpholino A Morpholino, also known as a Morpholino oligomer and as a phosphorodiamidate Morpholino oligomer (PMO), is a type of oligomer molecule (colloquially, an oligo) used in molecular biology to modify gene expression. Its molecular structure contains ...
s. The units of an oligomer may be connected by
covalent bond A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atom ...
s, which may result from bond rearrangement or
condensation reaction In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a ...
s, or by weaker forces such as
hydrogen bond In chemistry, a hydrogen bond (H-bond) is a specific type of molecular interaction that exhibits partial covalent character and cannot be described as a purely electrostatic force. It occurs when a hydrogen (H) atom, Covalent bond, covalently b ...
s. The term multimer () is used in biochemistry for oligomers of proteins that are not covalently bound. The major capsid protein VP1 that comprises the shell of polyomaviruses is a self-assembling multimer of 72 pentamers held together by local electric charges. Many
oil An oil is any nonpolar chemical substance that is composed primarily of hydrocarbons and is hydrophobic (does not mix with water) and lipophilic (mixes with other oils). Oils are usually flammable and surface active. Most oils are unsaturate ...
s are oligomeric, such as liquid paraffin.
Plasticizers A plasticizer (British English, UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity (physics), plasticity, to decrease its viscosity, and/or to decrease friction during its ...
are oligomeric
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s widely used to soften
thermoplastics A thermoplastic, or thermosoftening plastic, is any plastic polymer material that becomes pliable or moldable at a certain elevated temperature and solidifies upon cooling. Most thermoplastics have a high molecular weight. The polymer chains as ...
such as
PVC Polyvinyl chloride (alternatively: poly(vinyl chloride), colloquial: vinyl or polyvinyl; abbreviated: PVC) is the world's third-most widely produced synthetic polymer of plastic (after polyethylene and polypropylene). About 40 million tons o ...
. They may be made from monomers by linking them together, or by separation from the higher fractions of
crude oil Petroleum, also known as crude oil or simply oil, is a naturally occurring, yellowish-black liquid chemical mixture found in geological formations, consisting mainly of hydrocarbons. The term ''petroleum'' refers both to naturally occurring u ...
.
Polybutene Polybutene is an organic polymer made from a mixture of 1-butene, 2-butene, and isobutylene. Ethylene steam cracker C4s are also used as supplemental feed for polybutene. It is similar to polyisobutylene (PIB), which is produced from essential ...
is an oligomeric oil used to make
putty PuTTY () is a free and open-source terminal emulator, serial console and network file transfer application. It supports several network protocols, including SCP, SSH, Telnet, rlogin, and raw socket connection. It can also connect to a se ...
. Oligomerization is a chemical process that converts monomers to macromolecular complexes through a finite
degree of polymerization The degree of polymerization, or DP, is the number of structural unit, monomeric units in a macromolecule or polymer or oligomer molecule. For a homopolymer, there is only one type of monomeric unit and the ''number-average'' degree of polymeriza ...
.
Telomerization Telomerization is a reaction that produces a particular kind of oligomer with two distinct end groups. The oligomer is called a telomer. Some telomerizations proceed by radical pathways, many do not. A generic equation is: : where M is the monome ...
is an oligomerization carried out under conditions that result in
chain transfer In polymer chemistry, chain transfer is a polymerization reaction by which the activity of a growing polymer chain is transferred to another molecule: \ce^\bullet + \ce^\bullet where • is the active center, P is the initial polymer chain, X i ...
, limiting the size of the oligomers. (This concept is not to be confused with the formation of a
telomere A telomere (; ) is a region of repetitive nucleotide sequences associated with specialized proteins at the ends of linear chromosomes (see #Sequences, Sequences). Telomeres are a widespread genetic feature most commonly found in eukaryotes. In ...
, a region of highly repetitive DNA at the end of a
chromosome A chromosome is a package of DNA containing part or all of the genetic material of an organism. In most chromosomes, the very long thin DNA fibers are coated with nucleosome-forming packaging proteins; in eukaryotic cells, the most import ...
.)


Green oil

In the oil and gas industry, green oil refers to oligomers formed in all C2, C3, and C4 hydrogenation reactors of ethylene plants and other petrochemical production facilities; it is a mixture of C4 to C20 unsaturated and reactive components with about 90%
aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated (in which all ...
dienes and 10% of
alkanes In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in whi ...
plus
alkenes In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...
. Different heterogeneous and homogeneous catalysts are operative in producing green oils via the oligomerization of alkenes.


See also

*
GPCR oligomer A GPCR oligomer is a protein complex that consists of a small number ( ''oligoi'' "a few", ''méros'' "part, piece, component") of G protein-coupled receptors (GPCRs). It is held together by covalent bonds or by intermolecular forces. The subun ...
* Oligomery (botany) *
Protein oligomer Protein quaternary structure is the fourth (and highest) classification level of protein structure. Protein quaternary structure refers to the structure of proteins which are themselves composed of two or more smaller protein chains (also refe ...


References


External links

*{{Commonscatinline Polymer chemistry