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Racemization

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In chemistry racemization refers to partial conversion of one enantiomer into another.

Chiral molecules have two forms (at each point of asymmetry) which differ in their optical characteristics: the levorotatory form (the (−)-form) will rotate the plane of polarization of a beam of light to the left, while the dextrorotatory form (the (+)-form) will rotate the plane of polarization of a beam of light to the right. The two forms, which are non-superimposable mirror-images, are said to be enantiomorphic: each is the enantiomer of the other.

Many chemical processes take place without regard to a substance's optical characteristics, and result in a racemic mixture in which neither form predominates. However, pure forms of the enantiomers can be obtained: for example, by allowing crystallization, and hand-separating the left-handed and right-handed crystals. Biochemical reactions also prefer one enantiomer over another: most amino acids are enantiopure, and the L-form is used preferentially in biological systems.

Racemization is the process of an enantioenriched substance becoming a mixture of enantiomeric forms; the rate of racemization (from L-forms to a mixture of L-forms and D-forms) has been used as a way of dating biological specimens.

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Protein primary structure and posttranslational modifications
General: Protein biosynthesis | Peptide bond | Proteolysis | Racemization | N-O acyl shift
N-terminus: Acetylation | Formylation | Myristoylation | Pyroglutamate | methylation | glycation | myristoylation (Gly) | carbamylation
C-terminus: Amidation | Glycosyl phosphatidylinositol (GPI) | O-methylation | glypiation | ubiquitination | sumoylation
Lysine: Methylation | Acetylation | Acylation | Hydroxylation | Ubiquitination | SUMOylation | Desmosine | deamination and oxidation to aldehyde| O-glycosylation | imine formation | glycation | carbamylation
Cysteine: Disulfide bond | Prenylation | Palmitoylation
Serine/Threonine: Phosphorylation | Glycosylation
Tyrosine: Phosphorylation | Sulfation | porphyrin ring linkage | flavin linkage | GFP prosthetic group (Thr-Tyr-Gly sequence) formation | Lysine tyrosine quinone (LTQ) formation | Topaquinone (TPQ) formation
Asparagine: Deamidation | Glycosylation
Aspartate: Succinimide formation
Glutamine: Transglutamination
Glutamate: Carboxylation | polyglutamylation | polyglycylation
Arginine: Citrullination | Methylation
Proline: Hydroxylation
←Amino acids Secondary structure→
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