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Hydroxyproline and proline play key roles for collagen stability. [4] They permit the sharp twisting of the collagen helix. [ 5 ] In the canonical collagen Xaa-Yaa-Gly triad (where Xaa and Yaa are any amino acid), a proline occupying the Yaa position is hydroxylated to give a Xaa-Hyp-Gly sequence.
proline. Secondary amino acids, amino acids containing a secondary amine group are sometimes named imino acids, [2] [3] though this usage is obsolescent. [1] The only proteinogenic amino acid of this type is proline, although the related non-proteinogenic amino acids hydroxyproline [4] [5] [6] and pipecolic acid [7] have often been included in studies of this class of compounds.
Furthermore, proline is rarely found in α and β structures as it would reduce the stability of such structures, because its side chain α-nitrogen can only form one nitrogen bond. Additionally, proline is the only amino acid that does not form a red-purple colour when developed by spraying with ninhydrin for uses in chromatography. Proline ...
In protein, hydroxyproline is incorporated into protein by hydroxylation of proline. Pipecolic acid, a heavier analog of proline, is found in efrapeptin. Sarcosine is a N-methylized glycine so its methyl group is used in many biochemical reactions. Azetidine-2-carboxylic acid, which is a smaller homolog of proline in plants.
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Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride. [2] [3] Because proline is cheaply available in high optical purity, enantiomerically pure prolinol is also widely available.
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In enzymology, a proline 3-hydroxylase (EC 1.14.11.28) is an enzyme that catalyzes the chemical reaction. L-proline + 2-oxoglutarate + O 2 cis-3-hydroxy-L-proline + succinate + CO 2. The 3 substrates of this enzyme are L-proline, 2-oxoglutarate, and O 2, whereas its 3 products are cis-3-hydroxy-L-proline, succinate, and CO 2.
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