Z-Leu-Leu-Tyr-α-keto aldehyde
Need Assistance?
  • US & Canada:
    +
  • UK: +

Z-Leu-Leu-Tyr-α-keto aldehyde

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

Z-Leu-Leu-Tyr-α-keto aldehyde, an excellent inhibitor of serine and cysteine proteases, is an excellent inhibitor of chymotryptic-like activity of the proteasome with a Ki of about 3.0 nM. It may be valuable in identifying the role of the proteasome in the normal and abnormal pathways of protein catabolism in cells.

Category
Peptide Inhibitors
Catalog number
BAT-014409
CAS number
204649-66-1
Molecular Formula
C30H39N3O7
Molecular Weight
553.66
IUPAC Name
benzyl N-[(2S)-1-[[(2S)-1-[[(2S)-1-(4-hydroxyphenyl)-3,4-dioxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
Synonyms
L-Leucinamide, N-[(phenylmethoxy)carbonyl]-L-leucyl-N-[(1S)-1-[(4-hydroxyphenyl)methyl]-2,3-dioxopropyl]-; Z-LLY-α-keto aldehyde; N-[(Benzyloxy)carbonyl]-L-leucyl-N-[(2S)-1-(4-hydroxyphenyl)-3,4-dioxo-2-butanyl]-L-leucinamide; benzyl ((S)-1-(((S)-1-(((S)-1-(4-hydroxyphenyl)-3,4-dioxobutan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)carbamate; Cbz-Leu-Leu-Tyr-α-keto aldehyde
Appearance
Off-white Powder
Purity
≥95%
Density
1.188±0.06 g/cm3 (Predicted)
Boiling Point
813.3±65.0°C (Predicted)
Storage
Store at -20°C
Solubility
Soluble in DMSO
InChI
InChI=1S/C30H39N3O7/c1-19(2)14-25(28(37)31-24(27(36)17-34)16-21-10-12-23(35)13-11-21)32-29(38)26(15-20(3)4)33-30(39)40-18-22-8-6-5-7-9-22/h5-13,17,19-20,24-26,35H,14-16,18H2,1-4H3,(H,31,37)(H,32,38)(H,33,39)/t24-,25-,26-/m0/s1
InChI Key
HKFKZFVHAUUKCW-GSDHBNRESA-N
Canonical SMILES
CC(C)CC(C(=O)NC(CC1=CC=C(C=C1)O)C(=O)C=O)NC(=O)C(CC(C)C)NC(=O)OCC2=CC=CC=C2
1. Aldehydes, Aldehyde Metabolism, and the ALDH2 Consortium
Freeborn Rwere, Xuan Yu, Che-Hong Chen, Eric R Gross Biomolecules. 2022 May 30;12(6):763. doi: 10.3390/biom12060763.
The discovery of aldehydes dates back to 1774 when Carl Wilhelm Scheele synthesized acetaldehyde [...].
2. Microbial engineering for aldehyde synthesis
Aditya M Kunjapur, Kristala L J Prather Appl Environ Microbiol. 2015 Mar;81(6):1892-901. doi: 10.1128/AEM.03319-14. Epub 2015 Jan 9.
Aldehydes are a class of chemicals with many industrial uses. Several aldehydes are responsible for flavors and fragrances present in plants, but aldehydes are not known to accumulate in most natural microorganisms. In many cases, microbial production of aldehydes presents an attractive alternative to extraction from plants or chemical synthesis. During the past 2 decades, a variety of aldehyde biosynthetic enzymes have undergone detailed characterization. Although metabolic pathways that result in alcohol synthesis via aldehyde intermediates were long known, only recent investigations in model microbes such as Escherichia coli have succeeded in minimizing the rapid endogenous conversion of aldehydes into their corresponding alcohols. Such efforts have provided a foundation for microbial aldehyde synthesis and broader utilization of aldehydes as intermediates for other synthetically challenging biochemical classes. However, aldehyde toxicity imposes a practical limit on achievable aldehyde titers and remains an issue of academic and commercial interest. In this minireview, we summarize published efforts of microbial engineering for aldehyde synthesis, with an emphasis on de novo synthesis, engineered aldehyde accumulation in E. coli, and the challenge of aldehyde toxicity.
3. DNA-protein crosslink formation by endogenous aldehydes and AP sites
Jun Nakamura, Mai Nakamura DNA Repair (Amst). 2020 Apr;88:102806. doi: 10.1016/j.dnarep.2020.102806. Epub 2020 Feb 10.
Covalent binding between proteins and a DNA strand produces DNA-protein crosslinks (DPC). DPC are one of the most deleterious types of DNA damage, leading to the blockage of DNA replication and transcription. Both DNA lesions and endogenous products with carbonyl functional groups can produce DPC in genomic DNA under normal physiological conditions. For example, formaldehyde, the most abundant endogenous human carcinogen, and apurinic/apyrimidinic (AP) sites, the most common type of endogenous DNA lesions, has been shown to crosslink proteins and/or DNA through their carbonyl functional groups. Unfortunately, compared to other types of DNA damage, DPC have been less studied and understood. However, a recent advancement has allowed researchers to determine accurate yields of various DNA lesions including formaldehyde-derived DPC with high sensitivity and specificity, paving the way for new developments in this field of research. Here, we review the current literature and remaining unanswered questions on DPC formation by endogenous formaldehyde and various aldehydic 2-deoxyribose lesions.
Online Inquiry
Verification code
Inquiry Basket