Product Spotlight for 8/27/19: "Six Brilliant Little (Spot) Lights"

Instead of a single topic or item being featured in the Spotlight this week, we are combining some of our shorter "miniSpotlights" that we have posted on our website since the inaugural post in May, with the hopes that you will find something of interest.

Biologically Active Peptides

Substance P (PSP-4014-v, PSP-4014) is a member of the tachykinin neuropeptide family. The tachykinins have roles in nociception, pain, inflammation, and more recently in gut motility.1,2
Synonyms/Product Alternate Names: H-Arg-Pro-Lys-Pro-Gln-Gln-Phe-Phe-Gly-Leu-Met-NH2, RPKPQQFFGLM-NH2
New publication on Substance P: Substance P and Inflammatory Pain: Getting It Wrong and Right Simultaneously

  1. C. Severini, et al., Pharmacological Reviews, 54(2), 285 (2002).
  2. L. Palamiuc, et al., Nature Communications, 8, 14237 (2017).

OVA Peptide (257-264) (POV-3659-PI), or Chicken ovalbumin fragment (257-264),is T-cell activating peptide and the epitope from ovalbumin.
Synonyms/Product Alternate Names:H-Ser-Ile-Ile-Asn-Phe-Glu-Lys-Leu-OH, SIINFEKL
(related peptide: OVA Peptide (323-339), POV-3636-PI)
New publications on OVA (257-264):
Virus-specific memory T cells populate tumors and can be repurposed for tumor immunotherapy
Identification of epitopes in ovalbumin that provide insights for cancer neoepitopes

Lugdunin (LUG-3871-PI)is a “macrocyclic thiazolidine peptide antibiotic”. It is produced by the human nasal Staphylococcus lugdunensis strains and inhibits the colonization of Staphylococcus aureus. S. aureus, also known as “staph” bacteria, is often implicated in many human infections. Lugdunin may hold promise in the search for antibiotic alternatives, since current research suggests that it may be difficult for bacteria to develop a resistance to Lugdunin.1

Synonyms/Product Alternate Names: cyclo(D-Leu-Val-D-Val-2-[1S-1-amino-2-methylpropyl]-Thiapro-D-Val-Trp)
We recently came across an interesting publication on Lugdunin and analogues:
Synthetic Lugdunin Analogues Reveal Essential Structural Motifs for Antimicrobial Action and Proton Translocation Capability

From our archives: New and Improved Antimicrobial Peptides!
A. Zipperer, et al., Nature, 50, 511 (2016).

Enzyme Inhibitors and Substrates

E-64 (IES-4096, IES-4096-v) is an irreversible cysteine protease inhibitor. It reacts with the active site cysteine thiol to form a thioether. E-64 stimulates endothelial cell response to wounds1 and has been found to inhibit calpain, cathepsin B, H,and L, and papain, to name a few.
Synonym/Product Alternate Name: (L-3-trans-Ethoxycarbonyloxirane-2-Carbonyl)-L-Leucine (3-Methylbutyl)Amide

We also carry the analogs, E-64c (IEC-4320-v) and E-64d (IED-4321-v). E-64d is a potent and irreversible cathepsin B inhibitor with greater cell-permeability than E-64.
New publication mentioning E-64: Anionic Phospholipids Induce Conformational Changes in Phosphoenolpyruvate Carboxylase to Increase Sensitivity to Cathepsin Proteases
R. N. Mascardo & G. Eilon, Journal of Pharmacology and Experimental Therapeutics, 244 (1), 361(1988).

Tools for Peptide Synthesis

Fmoc-MeDbz (FMD-2331) is a useful linker in peptide synthesis, and, in particular, in preparing key C-terminal peptide thioester intermediates in native chemical ligation (NCL). The MeDbz group is also less prone to acetylation during sold-phase peptide synthesis (SPPS) than the first generation Nbz linker.

Synonym: 3-[(9-Flurenylmethyloxycarbonyl)Amino]-4-(Methylamino)Benzoic Acid
CAS Number: 1788861-35-7
J.B. B-Canosa, B. Nardone, F. Albericio, & P.E. Dawson, J. Am. Chem. Soc., 137, 7197 (2015).

Additional reading:Exploiting the MeDbz Linker to Generate Protected or Unprotected C‐Terminally Modified Peptides