Product Monographs
Bachem offers for free a series of brochures on selected groups of products in peptide research and detailed manuals on peptide synthesis.
Melanoma PeptidesMalignant melanoma is an increasingly important public health problem. The number of people who develop melanoma has more than doubled within the past 10 – 15 years. Presently, the incidence of melanoma rises 5 % per annum worldwide. Thus, melanoma represents the cancer that is rising faster than the incidence of any other “solid tumor” cancer. At an early stage melanoma is surgically completely curable, but recurrent or metastatic melanoma is often resistant to classical therapies and the prognosis of advanced melanoma is almost fatal. During the past years immune-based therapies were investigated as an adjuvant treatment of melanoma. The advantage of using the immune system to target and eliminate tumor cells is that only few side effects could be observed and an immunologic memory which provides a long-term protection against tumor recurrence or metastasis could be established. Meanwhile, important progresses have been obtained in the identification of melanoma-associated antigens which contain a significant number of epitopes that are recognized by cytotoxic T lymphocytes. However, the field of cancer vaccines is still in an early stage of development. In this monograph Bachem presents its melanoma peptides and melanoma-associated peptides for research purposes. |
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MMPMatrix Metalloproteinases The matrix metalloproteinases (MMPs) constitute a multigene family of over 25 secreted and membrane bound enzymes that degrade numerous pericellular substrates. Their targets include other proteinases, clotting factors, chemotactic molecules, latent growth factors, cell surface receptors, cell-cell adhesion molecules, and almost all structural extracellular matrix proteins. Thus, MMPs play a role in normal tissue modelling and differentiation during development. In pathological conditions they are involved in inflammation, degradation of bone, autoimmune diseases, and in the invasive migration of cancer cells across basement membrane as in tumor metastasis. To ascertain the role of a particular MMP in these disease states, it is desirable to have a series of synthetic substrates that allow a rapid discrimination of different MMP activities. |
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N-Methylated Amino AcidsN-Methylated amino acids are present in a wide variety of biological molecules such as complex molecular structures of certain microbial peptides and nucleic acid-binding proteins involved in gene regulation and gene expression. Methylation reactions generally increase the biochemical synthesis repertoire of cells and can serve as regulatory mechanisms. In pharmaceutical, chemical, and biological sciences, N-methylated amino acids can be used as building blocks for the design and synthesis of peptides with modified characteristics and therefore, find applications in drug discovery processes and structure activity relationship (SAR) studies. In this monograph, Bachem presents its N-methylated amino acids for peptide research. |
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Non-Ionic DetergentsDetergents are amphipathic molecules that contain both polar and hydrophobic groups. All detergents are characterized as containing a hydrophilic “head” region and a hydrophobic “tail” region. In contrast to purely polar or non-polar molecules, amphipathic molecules exhibit unique properties in water: Their polar group forms hydrogen bonds with water molecules, while the hydrocarbon chains aggregate due to hydrophobic interactions. These properties allow detergents to be soluble in water and also to solubilize hydrophobic compounds in water. |
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NPYNeuropeptide Y Neuropeptide Y (NPY) is one of the most abundant neuropeptides in the brain. Together with the two gut hormones, pancreatic polypeptide (PP) and peptide YY (PYY) it belongs to the pancreatic polypeptide hormone family, also known as the neuropeptide Y family. All three peptide hormones consist of 36 amino acid residues and are C-terminally amidated. This post-translational modification is essential for their biological activity. In addition to a distinct sequence homology they share a common hairpin-like three-dimensional structure, known as the pancreatic polypeptide fold (PP-fold). Neuropeptide Y exhibits a large number of physiological activities in the central and peripheral nervous system. These effects are mediated through the activation of Y receptors, which belong to the large superfamily of G-protein- coupled receptors (GPCRs). There is evidence that neuropeptide Y is implicated in the pathophysiology of a number of diseases such as feeding disorders and metabolic diseases as well as anxiety, seizures, intestinal dysfunction, cardiovascular, and respiratory diseases. Its various effects make neuropeptide Y to an attractive target for the potential treatment of several of these diseases. In this monograph Bachem presents a selection of its products in the field of neuropeptide Y (NPY) research. |
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OrthogonalityOrthogonality of Protecting Groups in Peptide Synthesis by Fmoc Strategy Fmoc/tBu probably is the most popular "orthogonal" combination of protecting groups. The term "orthogonal" was coined by Barany and Merrifield in 1977 as to designate "classes of protecting groups which are removed by differing chemical mechanisms. Therefore they can be removed in any order and in the presence of the other classes. Orthogonal protection schemes allow for milder overall reaction conditions as well as the synthesis of partially protected peptides" [G. Barany & R.B. Merrifield, J. Am. Chem. Soc. 99, 7363 (1977)]. The combination Fmoc/tBu is truly orthogonal whereas, e.g., Boc/OPp is not because both groups are acid-labile. As OPp can be removed selectively in the presence of Boc/tBu by "weak acid”, the combination has been termed "quasi-orthogonal". Modified peptides may be sensitive towards both bases and acids, so it should be kept in mind that Aloc/OAll and Z/Bzl may be removed under neutral conditions. Thus, when conceiving the synthesis of more complex or "modified" peptides (e.g. side-chain cyclized peptides), the tactics of synthesis, i.e. the choice of side-chain protecting groups and type of resin, has to be considered thoroughly. For on-resin modification Aloc/OAll, Dde/Dmab, Mtt/OPp may be selectively cleaved from peptides bound to Wang resin. The combination of these protecting groups allows the synthesis of very complex peptides, for an impressive example see R. Hirschmann et al., Tetrahedron 54, 7179 (1998). |
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PAR-Activating PeptidesProteinase-activated receptors (PARs) are a class of G-protein-coupled receptors consisting of four known members (PAR-1 to PAR-4). PARs are coupled to multiple signal transduction pathways and are involved in various physiological and pathophysiological processes including platelet activation, arterial thrombosis, inflammation and tumor progression. Receptor signaling is initiated by enzymatic cleavage at a specific site within the extracellular N-terminal domain of PARs by a serine protease. Proteolysis results in exposure of a tethered ligand domain that interacts with the receptor resulting in activation. Short synthetic peptide sequences corresponding to the tethered ligand motif of the proteolytically generated new N-terminal region can also bind to and activate PARs. In this monograph, Bachem offers a range of PAR-activating peptides and analogs useful for studying receptor function. |
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Peptide User GuideA brief introduction into synthesis methods, handling and design of peptides Decades of experience in peptide synthesis and the world’s largest group of peptide chemists in the industry make Bachem your ideal partner for the custom synthesis of peptides and complex organic molecules. Bachem offers a full range of technologies which are available at our production sites in the USA and in Europe. We produce research grade peptides as well as GMP-grade material, from simple peptides to the most complex peptidomimetics or synthetic proteins. Our experts will support you in the design of your peptides and peptide derivatives. The aim of this monograph is to present a general survey of the methods of peptide production, and to provide answers to the most frequently asked questions by the end user. This publication is focused on peptides used for research purposes (i.e. milligram to gram-scale). |
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Peptide YYPeptide YY (PYY) is a gut hormone which was first isolated in 1980 by Takemoto and coworkers from porcine intestine. It belongs to a structurally and functionally related family of peptides, which also includes neuropeptide Y (NPY) and pancreatic polypeptide (PP). The peptides of this family mediate their effects through several G protein-coupled receptors. PYY is primarily released from endocrine cells of the distal digestive tract and plays an important role in regulating gastrointestinal secretion and motility. Besides the major molecular form of PYY, also designated as PYY (1-36), which consists of 36 amino acid residues, a second aminoterminal truncated form of the peptide, PYY (3-36) could be detected in the blood. Both forms are bioactive but differ in their selectivity for the various receptor subtypes. Recently, a role in “long-term” regulation of food intake was suggested for PYY (3-36). In this monograph Bachem presents PYY and related peptides as well as immunochemicals for obesity research. |
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Peptides and DiabetesAccording to data from the International Diabetes Federation, more than 250 million people around the world suffer from diabetes mellitus, a chronic metabolic disorder characterized by hyperglycemia. Diabetes mellitus can be divided into two main types, type 1 or insulin-dependent diabetes mellitus (IDDM), and type 2, or non insulin-dependent diabetes mellitus (NIDDM). The absolute lack of insulin, due to destruction of the insulin-producing pancreatic β-cells, is the particular disorder in type 1 diabetes. Type 2 diabetes is mainly characterized by the inability of cells to respond to insulin. The condition affects mostly the cells of muscle and fat tissue, and results in a condition known as „insulin resistance“. Over time, diabetes mellitus can lead to blindness, kidney failure, and nerve damage. Diabetes mellitus is also an important factor in accelerating the hardening and narrowing of the arteries (atherosclerosis), leading to stroke, coronary heart diseases, and other blood vessel diseases. Glucose homeostasis is accomplished by complex physiological mechanisms. Control of blood glucose levels involves insulin, glucagon and other peptide hormones such as glucagon-like peptide 1 (GLP-1) and glucose-dependent insulinotropic polypeptide (gastric inhibitory polypeptide (GIP)). |
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