cyclo(L-Tyr-L-Val)

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Category Others
Catalog number BBF-04686
CAS 21754-25-6
Molecular Weight 262.3
Molecular Formula C14H18N2O3
Purity >95% by HPLC

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Description

Cyclo(L-Tyr-L-Val) is a diketopiperazine metabolite isolated from marine actinomycetes (Nocardiopsis gilva).

Specification

Synonyms Cyclo(Tyr-Val)
Storage Store at -20°C
IUPAC Name 3-[(4-hydroxyphenyl)methyl]-6-propan-2-ylpiperazine-2,5-dione
Canonical SMILES CC(C)C1C(=O)NC(C(=O)N1)CC2=CC=C(C=C2)O
InChI InChI=1S/C14H18N2O3/c1-8(2)12-14(19)15-11(13(18)16-12)7-9-3-5-10(17)6-4-9/h3-6,8,11-12,17H,7H2,1-2H3,(H,15,19)(H,16,18)
InChI Key LMDVFSHGYANGRP-UHFFFAOYSA-N

Properties

Solubility Soluble in ethanol, methanol, DMF, DMSO

Reference Reading

1. Cyclic peptides from an endophytic fungus obtained from a mangrove leaf (Kandelia candel)
Huarong Huang, Zhigang She, Yongcheng Lin, L L P Vrijmoed, Wenhan Lin J Nat Prod. 2007 Nov;70(11):1696-9. doi: 10.1021/np0605891. Epub 2007 Oct 19.
Two new cyclic depsipeptides, 1962A (1) and 1962B (2), along with the three known cyclodipeptides cyclo-(Leu-Tyr) (3), cyclo-(Phe-Gly) (4), and cyclo-(Leu-Leu) (5) were isolated from the fermentation broth of the mangrove endophytic fungus (No. 1962) isolated from an old leaf of Kandelia candel collected in Hong Kong. Through spectroscopic experimentation, X-ray crystallographic analysis, and acid hydrolysis followed by chiral HPLC analysis, their structures were established to be 1962A, cyclo-(D-Leu-Gly-L-Tyr-L-Val-Gly-S-O-Leu) (1), and 1962B, cyclo-(D-Leu-Gly-L-Phe-L-Val-Gly-S-O-Leu) (2), respectively. Both of these new cyclo-depsipeptides were found to contain one d-amino acid. In the MTT bioassay, 1962A (1) showed weak activity against human breast cancer MCF-7 cells.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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