An aminopolycarboxylic acid (sometimes abbreviated APCA) is a chemical compound containing one or more nitrogen atoms connected through carbon atoms to two or more carboxyl groups. Aminopolycarboxylates that have lost acidic protons form strong complexes with metal ions. This property makes aminopolycarboxylic acids useful complexone in a wide variety of chemical, medical, and environmental applications. [1]
The parent of this family of ligands is the amino acid glycine, H2NCH2COOH, in which the amino group, NH2, is separated from the carboxyl group, COOH by a single methylene group, CH2. When the carboxyl group is deprotonated the glycinate ion can function as a bidentate ligand, binding the metal centre through the nitrogen and one of two carboxylate oxygen atoms, to form chelate complexes of metal ions. [2]
Replacement of a hydrogen atom on the nitrogen of glycine by another acetate residue, –CH2COOH gives iminodiacetic acid, IDA, which is a tridentate ligand. Further substitution gives nitrilotriacetic acid, NTA, which is a tetradentate ligand. [3] These compounds can be described as aminopolycarboxylates. Related ligands can be derived from other amino acids other than glycine, notably aspartic acid.
Higher density is achieved by linking two or more glycinate or IDA units together. EDTA contains two IDA units with the nitrogen atoms linked by two methylene groups and is hexadentate. DTPA has two CH2CH2 bridges linking three nitrogen atoms and is octadentate. TTHA [1] has ten potential donor atoms.
The chelating properties of aminopolycarboxylates can be engineered by varying the groups linking the nitrogen atoms so as to increase selectivity for a particular metal ion. The number of carbon atoms between the nitrogen and carboxyl group can also be varied and substituents can be placed on these carbon atoms. Altogether this allows for a vast range of possibilities. Fura-2 combines two functionalities: it has high selectivity for calcium over magnesium and it has a substituent which makes the complex fluorescent when it binds calcium. This reagent provides a means of determining the calcium content in intra-cellular fluid. Details concerning applications of the following examples can be found in the individual articles and/or reference. The aminopolycarboxylate nicotianamine is widespread in plants, where it is used to transport iron.
 |  |  |  |
| glycinate | IDA [1] | NTA [3] | EDDA [3] |
 |  |  |  |
| EDTA | EDDS | DTPA [1] | EGTA |
 |  |  | |
| BAPTA | NOTA [1] | DOTA [1] | |
 |  | ||
| Nicotianamine [4] | EDDHA |
In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group attached to an R-group. The general formula of a carboxylic acid is often written as R−COOH or R−CO2H, sometimes as R−C(O)OH with R referring to an organyl group, or hydrogen, or other groups. Carboxylic acids occur widely. Important examples include the amino acids and fatty acids. Deprotonation of a carboxylic acid gives a carboxylate anion.
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 of the molecule's composition. This enables systematic prediction of chemical reactions and behavior of chemical compounds and the design of chemical synthesis. The reactivity of a functional group can be modified by other functional groups nearby. Functional group interconversion can be used in retrosynthetic analysis to plan organic synthesis.
Glycine is an amino acid that has a single hydrogen atom as its side chain. It is the simplest stable amino acid. Glycine is one of the proteinogenic amino acids. It is encoded by all the codons starting with GG. Glycine is integral to the formation of alpha-helices in secondary protein structure due to the "flexibility" caused by such a small R group. Glycine is also an inhibitory neurotransmitter – interference with its release within the spinal cord can cause spastic paralysis due to uninhibited muscle contraction.
In coordination chemistry, a ligand is an ion or molecule with a functional group that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electron pairs, often through Lewis bases. The nature of metal–ligand bonding can range from covalent to ionic. Furthermore, the metal–ligand bond order can range from one to three. Ligands are viewed as Lewis bases, although rare cases are known to involve Lewis acidic "ligands".
Chelation is a type of bonding of ions and their molecules to metal ions. It involves the formation or presence of two or more separate coordinate bonds between a polydentate ligand and a single central metal atom. These ligands are called chelants, chelators, chelating agents, or sequestering agents. They are usually organic compounds, but this is not a necessity.
Ethylenediaminetetraacetic acid (EDTA), also called EDTA acid, is an aminopolycarboxylic acid with the formula [CH2N(CH2CO2H)2]2. This white, slightly water-soluble solid is widely used to bind to iron (Fe2+/Fe3+) and calcium ions (Ca2+), forming water-soluble complexes even at neutral pH. It is thus used to dissolve Fe- and Ca-containing scale as well as to deliver iron ions under conditions where its oxides are insoluble. EDTA is available as several salts, notably disodium EDTA, sodium calcium edetate, and tetrasodium EDTA, but these all function similarly.
Metalloprotein is a generic term for a protein that contains a metal ion cofactor. A large proportion of all proteins are part of this category. For instance, at least 1000 human proteins contain zinc-binding protein domains although there may be up to 3000 human zinc metalloproteins.
An ylide or ylid is a neutral dipolar molecule containing a formally negatively charged atom (usually a carbanion) directly attached to a heteroatom with a formal positive charge (usually nitrogen, phosphorus or sulfur), and in which both atoms have full octets of electrons. The result can be viewed as a structure in which two adjacent atoms are connected by both a covalent and an ionic bond; normally written X+–Y−. Ylides are thus 1,2-dipolar compounds, and a subclass of zwitterions. They appear in organic chemistry as reagents or reactive intermediates.
In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is R−:C−R' or R=C: where the R represents substituents or hydrogen atoms.
In chemistry, a molecule or ion is called chiral if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality. The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property.
A transition metal carbene complex is an organometallic compound featuring a divalent carbon ligand, itself also called a carbene. Carbene complexes have been synthesized from most transition metals and f-block metals, using many different synthetic routes such as nucleophilic addition and alpha-hydrogen abstraction. The term carbene ligand is a formalism since many are not directly derived from carbenes and most are much less reactive than lone carbenes. Described often as =CR2, carbene ligands are intermediate between alkyls (−CR3) and carbynes (≡CR). Many different carbene-based reagents such as Tebbe's reagent are used in synthesis. They also feature in catalytic reactions, especially alkene metathesis, and are of value in both industrial heterogeneous and in homogeneous catalysis for laboratory- and industrial-scale preparation of fine chemicals.
Nitrilotriacetic acid (NTA) is the aminopolycarboxylic acid with the formula N(CH2CO2H)3. It is a colourless solid. Its conjugate base nitrilotriacetate is used as a chelating agent for Ca2+, Co2+, Cu2+, and Fe3+.
EDDHA or ethylenediamine-N,N′-bis(2-hydroxyphenylacetic acid) is a chelating agent. Like EDTA, it binds metal ions as a hexadentate ligand, using two amines, two phenolate centers, and two carboxylates as the six binding sites. The complexes are typically anionic. The ligand itself is a white, water-soluble powder. Both the free ligand and its tetraanionic chelating agent are abbreviated EDDHA. In contrast to EDDHA, most related aminopolycarboxylic acid chelating agents feature tertiary amines and few have phenolate groups.
In coordination chemistry, a stability constant is an equilibrium constant for the formation of a complex in solution. It is a measure of the strength of the interaction between the reagents that come together to form the complex. There are two main kinds of complex: compounds formed by the interaction of a metal ion with a ligand and supramolecular complexes, such as host–guest complexes and complexes of anions. The stability constant(s) provide(s) the information required to calculate the concentration(s) of the complex(es) in solution. There are many areas of application in chemistry, biology and medicine.
Iminodiacetic acid is the organic compound with the formula HN(CH2CO2H)2, often abbreviated to IDA. A white solid, the compound is a dicarboxylic acid amine (the nitrogen atom forms a secondary amino group, not an imino group as the name suggests). The iminodiacetate dianion is a tridentate ligand, forming metal complexes by forming two, fused, five membered chelate rings. The proton on the nitrogen atom can be replaced by a carbon atom of a polymer to create an ion-exchange resin, such as chelex 100. Complexes of IDA and EDTA were introduced in the early 1950s by Schwarzenbach.
DOTA (also known as tetraxetan) is an organic compound with the formula (CH2CH2NCH2CO2H)4. The molecule consists of a central 12-membered tetraaza (i.e., containing four nitrogen atoms) ring. DOTA is used as a complexing agent, especially for lanthanide ions. Its complexes have medical applications as contrast agents and cancer treatments.
In chemistry, binding selectivity is defined with respect to the binding of ligands to a substrate forming a complex. Binding selectivity describes how a ligand may bind more preferentially to one receptor than another. A selectivity coefficient is the equilibrium constant for the reaction of displacement by one ligand of another ligand in a complex with the substrate. Binding selectivity is of major importance in biochemistry and in chemical separation processes.
Trisodium N-(1-carboxylatoethyl)iminodiacetate, methylglycinediacetic acid trisodium salt (MGDA-Na3) or trisodium α-DL-alanine diacetate (α-ADA), is the trisodium anion of N-(1-carboxyethyl)iminodiacetic acid and a tetradentate complexing agent. It forms stable 1:1 chelate complexes with cations having a charge number of at least +2, e.g. the "hard water forming" cations Ca2+ or Mg2+. α-ADA is distinguished from the isomeric β-alaninediacetic acid by better biodegradability and therefore improved environmental compatibility.
Transition metal amino acid complexes are a large family of coordination complexes containing the conjugate bases of the amino acids, the 2-aminocarboxylates. Amino acids are prevalent in nature, and all of them function as ligands toward the transition metals. Not included in this article are complexes of the amides and ester derivatives of amino acids. Also excluded are the polyamino acids including the chelating agents EDTA and NTA.
Copper(II) glycinate (IUPAC suggested name: bis(glycinato)copper(II)) refers to the coordination complex of copper(II) with two equivalents of glycinate, with the formula [Cu(glycinate)2(H2O)x] where x = 1 (monohydrate) or 0 (anhydrous form). The complex was first reported in 1841, and its chemistry has been revisited many times, particularly in relation to the isomerisation reaction between the cis and trans forms which was first reported in 1890.