Phenylalanyl-histidine

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Phenylalanyl-histidine
Category Others
Catalog number BBF-05143
CAS 33367-37-2
Molecular Weight 302.33
Molecular Formula C15H18N4O3

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Description

Phenylalanylhistidine is a dipeptide composed of phenylalanine and histidine.

Specification

Synonyms Phe-his; L-phenylalanyl-L-histidine
Sequence H-Phe-His-OH
IUPAC Name (2S)-2-[[(2S)-2-amino-3-phenylpropanoyl]amino]-3-(1H-imidazol-5-yl)propanoic acid
Canonical SMILES C1=CC=C(C=C1)CC(C(=O)NC(CC2=CN=CN2)C(=O)O)N
InChI InChI=1S/C15H18N4O3/c16-12(6-10-4-2-1-3-5-10)14(20)19-13(15(21)22)7-11-8-17-9-18-11/h1-5,8-9,12-13H,6-7,16H2,(H,17,18)(H,19,20)(H,21,22)/t12-,13-/m0/s1
InChI Key OHUXOEXBXPZKPT-STQMWFEESA-N

Properties

Boiling Point 693.4±55.0°C at 760 mmHg
Density 1.3±0.1 g/cm3

Reference Reading

1. The amino acid composition of hypertensin II and its biochemical relationship to hypertensin I
K E LENTZ, L T SKEGGS Jr, K R WOODS, J R KAHN, N P SHUMWAY J Exp Med. 1956 Aug 1;104(2):183-91. doi: 10.1084/jem.104.2.183.
Preparations of hypertensin II, obtained from the treatment of hypertensin I by the action of the hypertensin converting enzyme of plasma and purified by countercurrent distribution, were quantitatively analyzed for their amino acid content. Chromatography on ion exchange columns showed the presence of equimolar amounts of aspartic acid, proline, valine, isoleucine, tyrosine, phenylalanine, histidine, and arginine. Hypertensin I was found to contain one mole of leucine and one mole of histidine in addition to the amino acids of hypertensin II. These two amino acids were isolated from the conversion products of hypertensin I and identified as the peptide histidylleucine. Carboxypeptidase digestion of hypertensin I showed the carboxyl terminal sequence of amino acids to be residue-phenylalanyl-histidylleucine. Similar studies of hypertensin II demonstrated residue-phenylalanine. It was concluded that the conversion of hypertensin I by the plasma hypertensin converting enzyme involved hydrolysis of the phenylalanyl-histidine bond to form hypertensin II and histidylleucine. The further removal by carboxypeptidase of phenylalanine from hypertensin II destroyed all of the vasoconstrictor activity.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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