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Z-Tyr-Val-Ala-Asp-AFC

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

The presence of halogen substituents on the fluorescent group improves the membrane permeability of YVAD-derived Caspase-1 substrate Z-YVAD-AFC.

Category

Others

Catalog number

BAT-015065

CAS number

201608-13-1

Molecular Formula

C39H40F3N5O11

Molecular Weight

811.76

Specification
Reference Reading

IUPAC Name

(3S)-3-[[(2S)-2-[[(2S)-2-[[(2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoyl]amino]-3-methylbutanoyl]amino]propanoyl]amino]-4-oxo-4-[[2-oxo-4-(trifluoromethyl)chromen-7-yl]amino]butanoic acid

Synonyms

L-a-Asparagine, N-[(phenylmethoxy)carbonyl]-L-tyrosyl-L-valyl-L-alanyl-N-[2-oxo-4-(trifluoromethyl)-2H-1-benzopyran-7-yl]-; N-[(Benzyloxy)carbonyl]-L-tyrosyl-L-valyl-L-alanyl-N-[2-oxo-4-(trifluoromethyl)-2H-chromen-7-yl]-L-α-asparagine; Caspase-1 Substrate (AFC); Z-YVAD-AFC

Appearance

White to Off-white Powder

Purity

≥90%

Density

1.411±0.06 g/cm3 (Predicted)

Boiling Point

1102.5±65.0°C (Predicted)

Sequence

Cbz-Tyr-Val-Ala-Asp-AFC

Storage

Store at -20°C

InChI

InChI=1S/C39H40F3N5O11/c1-20(2)33(47-36(54)28(15-22-9-12-25(48)13-10-22)46-38(56)57-19-23-7-5-4-6-8-23)37(55)43-21(3)34(52)45-29(18-31(49)50)35(53)44-24-11-14-26-27(39(40,41)42)17-32(51)58-30(26)16-24/h4-14,16-17,20-21,28-29,33,48H,15,18-19H2,1-3H3,(H,43,55)(H,44,53)(H,45,52)(H,46,56)(H,47,54)(H,49,50)/t21-,28-,29-,33-/m0/s1

InChI Key

QUINXAFKWYKRPT-FNGAAQSASA-N

Canonical SMILES

CC(C)C(C(=O)NC(C)C(=O)NC(CC(=O)O)C(=O)NC1=CC2=C(C=C1)C(=CC(=O)O2)C(F)(F)F)NC(=O)C(CC3=CC=C(C=C3)O)NC(=O)OCC4=CC=CC=C4

1. Release of IL-1beta via IL-1beta-converting enzyme in a skin dendritic cell line exposed to 2,4-dinitrofluorobenzene

Carlos B Duarte, M Celeste Lopes, Sara P Jaleco, Teresa J Matos, Margarida Gonçalo Mediators Inflamm . 2005 Aug 14;2005(3):131-8. doi: 10.1155/MI.2005.131.

We used a mouse fetal skin dendritic cell line (FSDC) to study the effect of the strong allergen 2,4-dinitrofluorobenzene (DNFB) on interleukin (IL)-1beta release and IL-1beta receptor immunoreactivity. Stimulation with DNFB (30 minutes) increased IL-1 release without changing the mRNA levels of the protein. Furthermore, DNFB increased transiently the interleukin-1beta-converting enzyme (ICE) activity, as measured with its fluorogenic substrate Z-Tyr-Val-Ala-Asp-AFC. The ICE inhibitor Z-YVAD-FMK prevented the release of IL-1beta evoked by DNFB. Incubation of the cells with DNFB (30 minutes) strongly increased IL-1beta receptor immunoreactivity. The rapid effect of DNFB on the release of mature IL-1beta, without inducing an increase of IL-1beta mRNA in FSDC, suggests a posttranslational modification of pro-IL-1beta by ICE activity.