cyclo(L-Ala-L-Leu)

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Category Others
Catalog number BBF-04684
CAS 24676-83-3
Molecular Weight 184.24
Molecular Formula C9H16N2O2
Purity >95% by HPLC

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Description

Cyclo(L-Ala-L-Leu) is a cyclic diketopiperazine found in fungi and bacteria. It has antiviral activity.

Specification

Storage Store at -20°C
IUPAC Name (3S,6S)-3-methyl-6-(2-methylpropyl)piperazine-2,5-dione
Canonical SMILES CC1C(=O)NC(C(=O)N1)CC(C)C
InChI InChI=1S/C9H16N2O2/c1-5(2)4-7-9(13)10-6(3)8(12)11-7/h5-7H,4H2,1-3H3,(H,10,13)(H,11,12)/t6-,7-/m0/s1
InChI Key DBJPZCJQDRPOME-BQBZGAKWSA-N

Properties

Antibiotic Activity Spectrum viruses
Solubility Soluble in methanol, DMSO

Reference Reading

1. Cyclic Dipeptides from Bacillus vallismortis BS07 Require Key Components of Plant Immunity to Induce Disease Resistance in Arabidopsis against Pseudomonas Infection
Seong Woo Noh, Rira Seo, Jung-Kwon Park, Md Maniruzzaman Manir, Kyungseok Park, Mee Kyung Sang, Surk-Sik Moon, Ho Won Jung Plant Pathol J. 2017 Aug;33(4):402-409. doi: 10.5423/PPJ.OA.11.2016.0255. Epub 2017 Aug 1.
Cyclic dipeptides (CDPs) are one of the simplest compounds produced by living organisms. Plant-growth promoting rhizobacteria (PGPRs) also produce CDPs that can induce disease resistance. Bacillus vallismortis strain BS07 producing various CDPs has been evaluated as a potential biocontrol agent against multiple plant pathogens in chili pepper. However, plant signal pathway triggered by CDPs has not been fully elucidated yet. Here we introduce four CDPs, cyclo(Gly-L-Pro) previously identified from Aspergillus sp., and cyclo(L-Ala-L-Ile), cyclo(L-Ala-L-Leu), and cyclo(LLeu-L-Pro) identified from B. vallismortis BS07, which induce disease resistance in Arabidopsis against Pseudomonas syringae infection. The CDPs do not directly inhibit fungal and oomycete growth in vitro. These CDPs require PHYTOALEXIN DEFICIENT4, SALICYLIC ACID INDUCTION DEFICIENT2, and NONEXPRESSOR OF PATHOGENESIS-RELATED PROTEINS1 important for salicylic acid-dependent defense to induce resistance. On the other hand, regulators involved in jasmonate-dependent event, such as ETHYLENE RECEPTOR1, JASMONATE RESPONSE1, and JASMONATE INSENSITIVE1, are necessary to the CDP-induced resistance. Furthermore, treatment of these CDPs primes Arabidopsis plants to rapidly express PATHOGENESIS-RELATED PROTEIN4 at early infection phase. Taken together, we propose that these CDPs from PGPR strains accelerate activation of jasmonate-related signaling pathway during infection.

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