Amino Acid Derivatives

α-Methyl-proline restores normal levels of bone collagen type I synthesis in ovariectomized rats, used as models for human postmenopausal osteoporosis.

The sequence RRPYIL is essential for neurotensin-NT receptor interaction.

Suc-YVAD-pNA, a chromogenic caspase-1 substrate.

<p>Bachem ID: 4096190.</p>

Substrate for aminopeptidase M, also used in histochemistry.

Inhibitor of tryptophan 5-monooxygenase.

IAPP 1-13 does not form fibrils, the region could be involved in the binding of amylin to membranes.

Cell-permeable nonaarginine amide, which can be easily conjugated to a cargo molecule, e.g. by maleimide-thiol coupling.

A highly sensitive fluorogenic substrate for the assay of human neutrophil and porcine pancreatic elastases. MeOSuc-AAPV-AMC is also cleaved by myeloblastin.

YGRKKRRQRRR, a cell-permeable peptide (CPP) derived from the HIV-1 tat protein transduction domain (PTD), has been shown to promote the entry of nucleic acids into several cell types.

Neuropeptide NPVF (VPNLPQRF-amide) is an endogenous anti-opioid peptide.

This synthetic oxytocin analog shows a prolonged effect due to an increased resistance to enzymatic cleavage. Carbetocin is highly effective in preventing post-partum hemorrhage after vaginal delivery.

FPA-pNA is cleaved by the sedolisins B, C, and D, tripeptidyl peptidases from Aspergillus fumigatus.

Tos-GPK-AMC, a fluorogenic substrate for trypsin, gingipain K, and cathepsin L.

<p>Bachem ID: 4030678.</p>

<p>Bachem ID: 4007899.</p>

Building block for the synthesis of aspartame analogs. CAS-Number (net): 40056-18-6.

The pyroglutamyl form of apelin-13 exhibited a high activity with an EC₅₀ value of 0.30 nM. pERPRLSHKGPMPF is probably the final product of the post-translational modification of apelin and the biologically active endogenous ligand. (Pyr¹)-Apelin-13 has been identified as the predominant apelin isoform in the human heart. Pyr-Apelin-13 stimulates glucose utilization in normal and obese insulin-resistant mice. It could be required for the maintenance of insulin sensitivity.

[1499-46-3] (net).

<p>Bachem ID: 4003323.</p>

<p>Bachem ID: 4012248.</p>

Non-mammalian Arg-vasopressin/oxytocin analog.

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

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

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

Deltorphin B, a selective δ-opioid receptor agonist isolated from the skin of Phyllomedusa bicolor.

Ac-DEVD-AFC is a sensitive fluorescent substrate for the assay of caspase-3 activity. The trifluoromethyl substituent of the fluorophore improves the membrane permeability of the substrate. CAS-Number (net) 141258-58-4 .

A synthetic chromogenic substrate for the determination of serinic and thiol proteases, e.g. urokinase, trypsin, cathepsin B, cathepsin L, and papain.

<p>Bachem ID: 4029233.</p>

Former CAS-number 26469-81-8.

Educt for the synthesis of proteasome inhibitors. Z-LL activates the ClpP protease from M. tuberculosis.

Z-GP-AMC, fluorogenic substrate for the determination of post-proline cleaving enzyme (prolyl endopeptidase).

Most circulating ghrelin is des-octanoyl ghrelin. The non-acylated ghrelin was considered inactive at first, though biological activities such as stimulation of adipogenesis and control of cell growth could be demonstrated more recently. Both ghrelin and the more abundant endogenous form des-octanoyl ghrelin could play a role in the paracrine regulation of vascular tone in humans.

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.

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.

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: 4001907.</p>

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

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

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.

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

Fluorophore-labeled phalloidin used for visualizing the actin cytoskeleton.

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

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.

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

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.

Competitive inhibitor of alanine racemase, Ki 0.005 mM.

A good substrate for carboxypeptidases B and N.

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.

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.

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.

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

Substrate for dipeptidyl aminopeptidase I (cathepsin C).

Substrate for porcine cathepsin A and acid carboxypeptidases from A. niger.and A. kawachii.

The oxytocin antagonist OVTA shows enhanced affinity for rat uterine oxytocin receptors after iodination.

N-terminal sequence of dynorphin A and the neoendorphins.

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.

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

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.

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

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

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

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.

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.

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).

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

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

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

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.

Muramyl dipeptide (MDP) inhibits HIV replication in CD4⁺ H9 lymphocytes..

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

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

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

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.

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).

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

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

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.

Active molecules as peptides can be readily conjugated to this cell-permeable peptide by the mercapto moiety.

Suc-AAPR-pNA, a substrate for wild-type and K188D/D189K trypsins (Km = 32.8 mM respectively 50.8 mM).

<p>Bachem ID: 4104812.</p>

PEG acrylate-based hydrogels have been modified with the RGD peptide YRGDS to improve their biocompatibility. YRGDS can be radioiodinated.

γ₁-MSH has been located in the cryptic region of the ACTH/β-lipotropin precursor protein from the intermediate lobe of bovine pituitary.

Apelin-17 is an endogenous ligand of the human orphan G protein-coupled receptor APJ, reported to act as a coreceptor of CD4 for human and simian immunodeficiency viruses. Apelin-17 and apelin-13 represent the predominant molecular forms of apelin present in the whole brain, hypothalamus, and plasma. Like apelin-13, apelin-17 exhibited a high activity on extracellular acidification rate and strongly inhibited forskolin-stimulated cAMP production in CHO cells expressing the human or the rat apelin receptor. The peptide might play a crucial role in the maintenance of body fluid homeostasis by counteracting AVP (arginine vasopressin) actions through inhibition of AVP neuron activity and AVP release.

DL-APNE (or NAPNE), a chromogenic substrate for chymotrypsin and microbial serine proteases, e.g. subtilisin. It is also hydrolyzed by cathepsin G. NAPNE was used by Yakoby and Raskin to determine the inhibitory activity of trypsin and chymotrypsin.

CPP for gene delivery.

Specific chromogenic substrate for cathepsin H.

<p>Bachem ID: 4096166.</p>

Impurity of tetracosactide, which is a synthetic peptide analog of the human adrenocorticotropic hormone that stimulates the production of cortisol.

A substrate for flavivirus proteases such as West Nile virus protease, yellow fever virus NS3 protease, and dengue virus NS2B-NS3 protease.Boc-GRR-AMC is cleaved by type II Metacaspases Atmc4 and Atmc9 of Arabidopsis thaliana. Stock solutions of Boc-GRR-AMC are best prepared in DMSO.

Suc-LLVY-pNA, chromogenic substrate analog to the proteasome substrate Suc-LLVY-AMC.

Diacetyl-Lys-D-Ala-D-Ala (DALAA) is a substrate for penicillin-sensitive D-alanine carboxypeptidases (DD-carboxypeptidases).

In search of competitive α-MSH antagonists, the hexapeptide GHRP-6 has been recognized as a selective inhibitor of α-MSH activity in the frog skin bioassay. It is identical in sequence with a growth hormone-releasing peptide analog, (His¹,Lys⁶)-GHRP, which selectively releases GH in vitro and in a wide variety of species in vivo. GHRP-6 also acts as a functional antagonist of somatostatin in the somatotrope cells.

Z-GGL-AMC, a fluorogenic substrate for the chymotrypsin-like activity of the 20S proteasome. Sensitive fluorogenic substrate for subtilisins BPN’ and Carlsberg. Also cleaved by ClpP protease from M. tuberculosis.

Special fluorogenic substrate for aminopeptidase M (microsomal alanyl aminopeptidase, membrane aminopeptidase, APN). Furthermore, the major aminopeptidase from human skeletal muscle showed highest activity with this substrate.

<p>Bachem ID: 4027358.</p>

Ac-RGK(Ac)-AMC, fluorogenic substrate for assaying histone deacetylase (HDAC) activity in a two-step enzymatic reaction. The assay consists of the initial lysine deacetylation by HDAC followed by the release of the fluorescent group by trypsin.

<p>Bachem ID: 4002971.</p>

Excitatory amino acid neurotransmitter. NMDA is a selective agonist of the glutamate receptor that regulates Ca²⁺ channels.

Substrate for FK-506 binding proteins (FKBPs, also called macrophilins) and cyclophilins, which belong to the group of peptidyl prolyl cis-trans isomerases (PPIases). Suc-AFPF-pNA has been used for an uncoupled protease-free assay of PPIase activity.

Fmoc-D-AzF can be incorporated in peptides as precursor of p-aminophenylalanine. Levinson et al. reduced the azido group on-resin with a large excess of tributylphosphine in DMF.

A good substrate for carboxypeptidase Y. Educt for the synthesis of fluorinated α-keto carboxylic inhibitors of chymotrypsin published by Parisi and Abeles.

<p>Bachem ID: 4012160.</p>