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Key Documents

SMB00934

Sigma-Aldrich

Cyclo(-Phe-Pro)

≥95% (HPLC)

Synonym(s):

Cyclo(-Phe-Pro), Cyclo(L-Phe-L-Pro), Cyclo-L-phenylalanyl-L-proline

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About This Item

Empirical Formula (Hill Notation):
C14H16N2O2
CAS Number:
3705-26-8
Molecular Weight:
244.29
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

200

Assay

≥95% (HPLC)

form

solid

color

off-white

storage temp.

2-8°C

InChI

1S/C14H16N2O2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12H,4,7-9H2,(H,15,17)/t11-,12-/m0/s1

InChI key

QZBUWPVZSXDWSB-RYUDHWBXSA-N

General description

Cyclo(Phe-Pro) is a secondary metabolite produced by human pathogen Vibrio vulnificus and some other bacteria including Lactobacillus species that exhibit potent antifungal activates. Also, cyclo(Phe-Pro) displays cytotoxic activity against HCT-116 cells. Cyclo(Phe-Pro) function as a quorum sensing agent in Vibrio vulnificus.

Application

Metabolomics research

Other Notes

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Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Can Chen et al.
Frontiers in microbiology, 9, 1587-1587 (2018-08-04)
A new bacterial strain, designated 452T, was isolated from the rhizosphere soil of the mangrove Avicennia marina in China. As determined, its cell wall peptidoglycan contained LL-diaminopimelic acid; MK-9(H8) and MK-9(H6) were the major isoprenoid quinones; and iso-C16:0 (31.3%), anteiso-C15:0
Katrin Ström et al.
Applied and environmental microbiology, 68(9), 4322-4327 (2002-08-30)
We have isolated a Lactobacillus plantarum strain (MiLAB 393) from grass silage that produces broad-spectrum antifungal compounds, active against food- and feed-borne filamentous fungi and yeasts in a dual-culture agar plate assay. Fusarium sporotrichioides and Aspergillus fumigatus were the most
Wooseong Lee et al.
Nature communications, 9(1), 1606-1606 (2018-04-25)
The recognition of pathogen-derived ligands by pattern recognition receptors activates the innate immune response, but the potential interaction of quorum-sensing (QS) signaling molecules with host anti-viral defenses remains largely unknown. Here we show that the Vibrio vulnificus QS molecule cyclo(Phe-Pro)

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