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peptide

peptide, organic compound composed of amino acids linked together chemically by peptide bonds. The peptide bond always involves a single covalent link between the α-carboxyl (oxygen-bearing carbon) of one amino acid and the amino nitrogen of a second amino acid. In the formation of a peptide bond from two amino acids, a molecule of water is eliminated. Small peptides with fewer than about ten constituent amino acids are called oligopeptides, and peptides with more than ten amino acids are termed polypeptides. Compounds with molecular weights of more than 10,000 (50–100 amino acids) are usually termed proteins. Organisms commonly contain appreciable quantities of low-molecular-weight peptides some arising from proteins while others are synthesized directly. Certain of these molecules are unusual in that they incorporate amino acids not found in proteins such as amino acids of the d -configuration. Among the biological peptides are many with physiological or antibacterial activity, such as the peptide hormones oxytocin and vasopressin; adrenocorticotropic hormone (ACTH), secreted by the pituitary gland; and several cyclic peptides, in which the amino-acid sequence forms a ring structure rather than a straight chain, such as the antibiotics tyrocidin and gramicidin. Laboratory synthesis of peptides has risen to the level of a well-defined art in recent years. Synthetic peptides, composed of as many as a hundred amino acids in specified sequence, have been prepared in the laboratory with good purity and high yields.

The Columbia Electronic Encyclopedia, 6th ed. Copyright © 2012, Columbia University Press. All rights reserved.

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