Amino Acid Derivatives

<p>This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Sci</p>

<p>gamma-L-Glutamyl hydrazide</p>

<p>Endogenous opioid neurotransmitter that is an agonist at mu- and delta-opioid receptors</p>

<p>L-Histidine methyl ester dihydrochloride is used to prepare optically pure L-(+)-ergothioneine. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar prod</p>

Suc-AAA-pNA, a readily soluble and sensitive substrate for human and rat neutrophil and porcine pancreatic elastases. The trialanine substrate is also hydrolyzed by proteinase K, subtilisins and thermitase as well as by astacin, a crayfish zinc-endopeptidase.

A good substrate for carboxypeptidases B and N.

Competitive inhibitor of alanine racemase, Ki 0.005 mM.

Arginine oligomers as heptaarginine, either alone or when conjugated to therapeutic agents or large biopolymers, have been shown to cross readily a variety of biological membranes (e.g. lipid bilayers and epithelial tissue). The importance of the guanidinium group in transport was supported by the observation that short oligomers of arginine entered cells far more rapidly than the corresponding oligomers of either lysine, histidine, ornithine, or citrulline.

The peptidylprolyl isomerase substrate Suc-AAPF-AMC is also hydrolyzed by carboxypeptidase Y, cathepsin G, and chymotrypsin. Suc-AAPF-AMC has also been used to analyze the chymotrypsin-like activity of trypsins.

<p>Bachem ID: 4001907.</p>

<p>Bachem ID: 4007171.</p>

α-Melanotropin, also known as α-melanocyte-stimulating hormone (α-MSH), is a 13-amino acid peptide originally characterized as a neuropeptide derived from the pituitary gland. α-MSH is synthesized from pro-opiomelanocortin (POMC) by the action of specific prohormone convertases and is involved in the regulation of important physiological functions including food intake, energy homeostasis, modulation of immune responses and photoprotection.

The presence of halogen substituents at the fluorescent group improves membrane permeability of the YVAD-derived caspase-1 substrate.

Fluorophore-labeled phalloidin used for visualizing the actin cytoskeleton.

Potent and long-acting CRF antagonist.

KALA amphipathic peptide, a low-molecular weight cationic amphipathic peptide was able to bind to DNA, to destabilize membranes and to mediate transfection of plasmid DNA in various cell lines. Thus, KALA provides a starting point for a family of peptides that incorporate other functions to improve DNA delivery systems.

Iberiotoxin (IbTx), from the venom of the scorpion Buthus tamulus, shows 68% sequence homology with charybdotoxin, another scorpion-derived peptidyl toxin. Although these two toxins both inhibit the high conductance Ca²⁺ activated K⁺ channel, they appear to bind at different sites on the channel and modulate channel activity by different mechanisms. Thus, iberiotoxin can be used to selectively study the function of the high conductance Ca²⁺ activated K⁺ channel.

In vitro, this compound competitively inhibited sweetalmond β-glucosidase (Ki = 17 µM).

Thymopentin (TP5), an active fragment of thymopoietin (TP), reduces endocrine and behavioral responses to experimental stress, possibly by lowering plasma TP (pTP) levels. The immunomodulatory peptide suppresses proliferation and induces differentiation in HL-60 cells.

<p>Bachem ID: 4029353.</p>

Sensitive fluorogenic substrate for trypsin, soybean trypsin-like enzyme, and papain.

Substrate for assays of aminopeptidase M and leucine aminopeptidase. Its use for histochemical purposes has been described.

Vasotocin (AVT, argiprestocin) is the vasopressin/oxytocin analog produced in birds, amphibians and fish. AVT shows antidiuretic as well as reproductive activities.

Sensitive fluorogenic substrate for dipeptidyl aminopeptidase I (DPP I, cathepsin C).

Suc-AAA-AMC, sensitive fluorogenic substrate for pancreatic elastase.

Z-VAD(OMe)-FMK, a pan-caspase inhibitor, is a competitive irreversible peptide inhibitor and blocks caspase-1 family and caspase-3 family enzymes. The methyl ester of Z-VAD-FMK has been used in studies to support the hypothesis that inhibitors of caspases can limit brain infarction resulting from the permanent obstruction of a brain artery.

<p>Bachem ID: 4068086.</p>

Orexin A (OXA, hypocretin-1) is a hypothalamic neuropeptide regulating the feeding behavior. Central administration of orexin A to rats stimulated food consumption in a dose-dependent manner. The effect persisted at 4 h after injection, as orexin A seems to be resistant to peptidases. Orexin A specifically binds a G protein-coupled receptor, OX₁R (IC₅₀ = 20 nM to displace 50 % of radiolabeled orexin A bound to this receptor). Orexin A produced in the amygdala induces wakefulness and plays a role in the induction of human emotions. Narcolepsy has been associated with orexin deficiency. The peptide also corresponds to bovine, canine, ovine, and porcine orexin A.

Rat pTH (1-34) suppressed appositional bone formation by cultured rat cranial osteoblasts.

FAM-HIV-1 Tat 47-57 was used as a fluorescent probe for studying the interaction between the p53 tetramerization domain and HIV-1 Tat protein.

<p>Bachem ID: 4034491.</p>

<p>Bachem ID: 4012616.</p>

The major regulator of adrenal cortex function. ACTH stimulates the synthesis of steroidal hormones.

Endogenous kappa-opioid receptor agonist. It is suggested that it attenuates galanin-induced impairment of memory processes through the mediation of kappa-opioid receptors.

<p>Bachem ID: 4004112.</p>

CALP-3, VKFGVGFK, acts as a calmodulin agonist. The octapeptide interacts with the calmodulin EF-hand motif, the Ca²⁺-binding site. CALP-3 activates phosphodiesterase in the absence of calcium and inhibits Ca²⁺-mediated cytotoxicity and apoptosis. CALP-3 is more active than CALP-1. By preventing trypsin activation within pancreatiic acinar cells CALP-3 shows potential therapeutic potential in the treatment of pancreatitis.

pTH (1-31) amide appears so far to be the smallest of the potently osteogenic pTH fragments. The osteogenic activity of this pTH fragment seems to be related to its ability to activate adenylyl cyclase. Unlike pTH, this fragment does not activate phospholipase C and should therefore have fewer side-effects and find application in the osteoporosis treatment.

The histone fragment was used as substrate for the protein arginine methyltransferase PRMT4.

Non-mammalian Arg-vasopressin/oxytocin analog.

This pTHrP fragment stimulated membrane-associated protein kinase C in freshly isolated rat spleen lymphocytes and thus raises the possibility of being a physiological regulator of the proliferation and other activities of lymphocytes.

Gluten Exorphin C, isolated from the pepsin-trypsin-chymotrypsin digest of wheat gluten, was considered as a δ-opioid receptor-selective ligand. The hydrophobicity of Ile³ seems to be important for the expression of the opioid activity of gluten exorphin C. Moreover, this peptide appears to be quite different from any of the endogenous and exogenous opioid peptides ever reported as the N-terminal Tyr is the only aromatic amino acid in the structure.

V.Paspaliaris et al. showed that daily administration of pTHrP (1-34) to rats was anabolic on bone by increasing bone formation. This treatment could inhibit the rapid decline in bone formation due to denervation.

<p>Bachem ID: 4051303.</p>

Potential degradation product of exenatide resulting from aspartimide formation and cleavage.

The pentadecapeptide BPC-157 (GEPPPGKPADDAGLV) shows a protective effect on stomach and duodenum when administered to stress ulcers, cysteamine-duodenal ulcers and ethanol lesions. Application of BPC 157 improved tendon healing.

This product is used for the attachment of the FLAG-tag by copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC), the prototypical reaction of click chemistry, as described for example by Wang and coworkers. In addition, Azido-PEG3-FLAG contains a PEG-linker. The resulting FLAG-tagged molecules can be detected or purified immunologically, using dye labeled, enzyme coupled or, for purification, immobilized anti-FLAG antibodies.

The pTHrP-analog abaloparatide (BIM-44058) promoting bone growth has been developed for the treatment of osteoporosis.

As antagonist of CCK, PP inhibits pancreatic sedretion. PP also acts on the gastrointestinal motility, food intake, and metabolism.