Amino Acid Derivatives

<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>

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

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

<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>

GRF antagonist.

RR-AMC, fluorogenic substrate for dipeptidyl peptidase III (DPP III).

Substrate for aminopeptidase M and leucine aminopeptidase.

Human ghrelin (GHR), the endogenous ligand of the growth hormone secretagogue receptor (GHS-R), potently stimulates GH release. The Ser³ octanoyl ester turned out to be essential for generating this activity. Ghrelin plays an important role in the short-time regulation of appetite and in the long-time regulation of energy balance and glucose homeostasis. A number of studies showed that ghrelin is also involved in the regulation of gastrointestinal, cardiovascular, and immune functions as well as in bone metabolism.

Suc-AAVA-pNA has been used for assaying hamster chymase 2.

AAF-AMC, fluorogenic substrate for tripeptidyl peptidases I and II and for tripeptide aminopeptidase EC 3.4.11.4.

A ghrelin receptor antagonist. Asakawa et al. found that peripherally administered (D-Lys³)-GHRP-6 (HwkWfK-amide) decreased food intake in lean mice, in mice with diet induced obesity, and in ob/ob obese mice, and that repeated administration of this GHS-R antagonist decreased body weight gain and improved glycaemic control in ob/ob obese mice.

The peptide hormone osteocalcin is involved not only in bone formation, it also plays an important role in glucose metabolism and could regulate testosteron. In mice, only the completely decarboxylated form of the peptide shows the latter hormonal activities, whereas in humans, osteocalcin, partially decarboxylated osteocalcins, and the uncarboxylated peptide seem to be involved. Generally, obese individuals have been shown to have lower osteocalcin(s) levels than non-obese controls, and type 2 diabetic individuals have lower plasma osteocalcin than non-diabetic individuals.

Deamidation product of glucagon.

Glucagon-Like Peptide 1 (GLP-1) is synthesized by posttranslational processing of proglucagon in the intestine and pancreas and plays an important role in metabolic homeostasis. Among the different molecular forms, such as GLP-1 (7-36) amide and GLP-1 (7-37), the function of GLP-1 (1-37) has been unclear. GLP-1 (1-37) was shown to convert intestinal epithelial cells into insulin-producing cells. These observations turned GLP-1 (1-37) into a new promising therapeutic compound for the treatment of diabetes mellitus. In animal models of dilated cardiomyopathy, hypertensive heart failure, and myocardial infarction, GLP-1 has shown a remarkable cardioprotective activity.

Peptide YY has been isolated from human colonic extracts. It is identical in sequence to porcine PYY except for two amino acid replacements.

In contrast to the octanoylated peptide, the non-acylated ghrelin does not activate growth hormone secretagogue receptor-expressing cells. The peptide decreases food intake and gastroduodenal motility in conscious rats, probably by crossing the blood-brain barrier and activating the brain receptor directly.

Suc-AAPL-pNA, a sensitive substrate for human and especially porcine pancreatic elastases. Substrate for leucine endopeptidase from the psychrotropic bacillus B. cereus.

<p>Bachem ID: 4002476.</p>

CTAP, an analog of CTOP, is a selective µ-opioid receptor antagonist.

A specific substrate for dipeptidyl aminopeptidase IV (DPP IV). Gly-Pro-MNA is very suitable for histochemical purposes.

Leu-OMe (LME) causes lysosomal disruption and death of human monocytes (M phi). In addition, LME removed natural killer cell (NK) activity from human peripheral mononuclear cells (PBM). During incubation of human lymphocytes with Leu-OMe, the dipeptide Leu-Leu-OMe which is responsible for the NK-toxicity, is formed.

Ac-DEVD-CMK irreversibly inhibits caspase-3. It is also active towards caspases-6, -7, -8, and -10.

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

Bz-VGR-AMC has been employed as substrate for the tricorn core protease from Thermoplasma acidophilum. Bz-VGR-AMC is used for measuring the trypsin-like activity of the 20S proteasome, in combination with e.g. Suc-LLVY-AMC (for assaying its chymotrypsin-like activity) and Z-LLE-AMC (for determining its PGPH activity).

Fluorogenic substrate for farnesyl diphosphate farnesyltransferase (FTase). The pentapeptide is based on the C-terminal region of H-Ras with a dansyl group attached to the N-terminus. Due to farnesylation of the cysteine thiol group the dansyl group is placed from a polar to a non-polar molecular environment which is accompanied by an enhancement of fluorescence and a shift to a lower wavelength emission maximum of the dansyl group. Complete conversion of the product results in a decrease of the emission maximum wavelength from 565 nm to 515 nm together with a 13-fold enhancement in fluorescence intensity at 505 nm. Dansyl-GCVLS can be used for continuously monitoring FTase activity in the presence of farnesyl diphosphate (FPP) at 505 nm using an excitation wavelength of 340 nm (kcat = 0.5 s⁻¹; Km = 1.4 µM). It represents a useful tool for screening potential FTase inhibitors. The substrate is highly specific to FTase and is not recognized by geranylgeranyl transferse type I (GGTase I). Concentrations of stock solutions of Dns-GCVLS can be calculated from the extinction coefficient of the dansyl moiety (ε₃₄₀ = 4250 M⁻¹cm⁻¹ in 20 mM Tris-HCl, pH 7.5, 10 mM EDTA).

Nafarelin is a synthetic decapeptide agonist of the luteinizing hormone-releasing hormone (LHRH) which is approximately 200 times more potent than the natural peptide. Like LHRH nafarelin stimulates the release of the gonadotrophins luteinizing hormone (LH) and follicle stimulating hormone (FSH) from the anterior pituitary which in turn results in an initial increase of testosterone and estradiol synthesis. Continuous administration of LHRH or one of its analogs causes a sustained down-regulation of circulating LH and FSH levels leading to a suppression of testicular and ovarian steroidogenesis. Currently, nafarelin is indicated for the treatment of endometriosis and for the use in reproductive medicine. CAS Number (nafarelin acetate): 86220-42-0.

Hymenistatin I (HS-I) exerts an immunosuppressive effect in the humoral and cellular immune responses comparable with that of cyclosporin A (CsA). Comparison of the influence of HS-I and CsA on cytokine production suggests that the mechanisms of the interaction with the immunological system are substantially different for the two compounds tested.

Substrate for human plasma carboxypeptidase N and membrane-bound carboxypeptidase D.

AFP-pNA, substrate for prolyl tripeptidyl aminopeptidases from the periodontal pathogens Porphyromonas gingivalis and Prevotella nigrescens.

A hypothalamic neuropeptide which stimulates the release of LH and FSH. CAS Number (gonadorelin acetate): 34973-08-5.

<p>Bachem ID: 4014443.</p>

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.

The pentapeptide TRSAW, a highly conserved sequence within the pTH-related protein, is a potent inhibitor of osteoclastic bone resorption in vitro (EC₅₀ = 10⁻¹⁵ M).

Tetraproline. PPPP was used as an internal standard in the quantitative determination of the antihypertensive (ACE-inhibiting) peptides IPP and VPP in cheese by HPLC-MS³.

Caloxin 2A1 is a selective extracellular inhibitor of the plasma membrane Ca²⁺-pump.

<p>Bachem ID: 4011476.</p>

<p>Bachem ID: 4015469.</p>

CPP for gene delivery.

<p>Bachem ID: 4013891.</p>

This peptide is the pp60 c-src carboxy-terminal phosphoregulatory peptide phosphorylated at Tyr⁵²⁷. The peptide fragment is involved in the regulation of kinase activity by binding intramolecularly or intermolecularly to the SH2 domain of the pp60 c-src protein.