• MSDS:
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Peptide Synthesis 1. Introduction

Author:N/A    | Post time:2012-05-26

1. Introduction
Top of page
1. Introduction
2. Fundamentals of Peptide Synthesis
3. Strategies for Peptide Synthesis
4. Chain-Growing and Side-Chain Protective Groups
5. Coupling Methods
6. Side Reactions
7. Summary and Outlook
Whenever we eat proteins, digestive enzymes (proteases) cleave these proteins to smaller entities that are called peptides. The word peptide (Greek:        = peptos = digested) reflects this fact because it means “small digestible”. Both, proteins and peptides, are polymers that are formed by the consecutive addition of different monomeric building blocks, namely the 20 natural amino acids (  Proteins;   Enzymes, 1. General;   Amino Acids). The distinction between a peptide and a protein is somewhat arbitrary. The most accepted convention draws the line that distinguishes a protein from a peptide at around 50 amino acids:
Natural peptides perform many different functions in the organism, e.g.:
Peptide hormons like insulin or glucagon regulate cell metabolism;
Defensins (peptidic antibiotics) shield a frog\'s skin and our gut from infections;
Small peptides loaded onto peptide-presenting proteins (MHC molecules) on the surface of every cell from a higher organism report to the immune system if the cell was captured by a virus. If recognized by a T-cell receptor, these peptides are called T-cell epitopes. These are the most important components of a vaccine.
Larger proteins are usually assembled from several smaller domains that quite often function on their own if separated from the other moieties. For example, a functional building block for an antibody protein (Ig domain) is about 100 amino acids long, whereas a zinc-finger domain that specifically binds to a short sequence of DNA typically comprises approximately 30 amino acids.
Due to the plethora of functions that proteins and peptides exert in the organism, especially the life sciences strive to isolate these molecules in high purity and in large quantities to test them for function. In addition, peptides increasingly get into the focus of pharmaceutical applications:
A peptide that binds to a disease-specific antibody might be a diagnostic marker;
A peptide that is recognized by a T-cell receptor might be a vaccine; and
A peptide that binds to and thereby inhibits a protein within a signaling cascade might be useful for basic research and eventually for therapeutic intervention.
Examples for peptides already used as drugs are given in Table 1.
Table 1. Peptide-based drugs
Name/trade name (company) Use (Number of amino acids) description

(Roche) HIV-1 infection (37)

inhibits the fusion of HIV with the target cell; used in combination therapy
Goserelin acetate/Zoladex

(AstraZeneca) breast and prostate cancer (9)

suppresses production of testosterone and estrogen
Bivalirudin/Angiomax, Angiox

(The Medicines Company) thrombotic process (23)

anticoagulant, thrombin inhibitor

(Eli Lilly) osteoporosis (34)

recombinant form of parathyroid hormone

(Jerini/Shire) hereditary angioedema (10)

antagonist of bradykinin B2 receptors

(Millennium Pharmaceuticals) acute cardiac ischemic events (7, cyclic)

found in the venom of the southeastern pygmy rattlesnake

(Novartis) post-allogeneic organ transplant (11, cyclic)

immunosuppressant, reduces risk of organ rejection

(Eli Lilly) diabetes mellitus type 2 (39)

regulates the glucose metabolism and insulin secretion
Vancomycin, Sandostatin

(Novartis) Gram-positive bacteria infections tricyclic glycosylated antibiotic peptide, produced by the fermentation of Amycolatopsis orientalis
Glatiramer acetate/Copaxone

(Teva Pharmaceuticals) multiple sclerosis random polymer (Mr ca. 6400) made of four amino acids


(Novartis) hypercalcemia, osteoporosis (32) linear polypeptide

diagnostically used as tumor marker for thyroid cancer
Insulin and insulin analogs

(many suppliers) diabetes mellitus type 1 (21 A-chain and 30 B-chain)

generated from 81amino acids long proteolytically cleaved proinsulin

Especially for pharmaceutically relevant assays, the scientist needs to get hold on many different peptides or proteins, which is the main incentive for the development of high-density protein and peptide arrays.
There are four procedures to get hold of proteins and peptides:
Extract them from natural sources;
Express them recombinantly by genes smuggled into microorganisms;
Synthesize them with the help of a cell lysate (and a cell\'s ribosome) outside a cell; and
Synthesize them chemically.
In contrast to the other procedures, chemical synthesis allows for the incorporation of unnatural amino acids, d-amino acids, and other building blocks, and for the production of large quantities with high quality. Of course, chemistry also helps synthesize natural peptides that are difficult to express in living systems. Only the chemical synthesis is the topic of this article.

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