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Literature > Technical Bulletins

Here you will find all the latest technical bulletins on Carbosynth's featured products. Click to download the pdf files.


Human Milk Oligosaccharides

Human breast milk provides the primary source of nutrition for newborns before they are able to eat and digest other foods. One distinctive property of human milk from most other species is the amount and diversity of the free oligosaccharide it contains. Currently at least 130 unique HMO have been identified, all differing by constituent sugars, molecular weight or structure. 

Lewis Sugars

The antigens of the Lewis system are carbohydrate determinants carried either on proteins or lipids. Although they were first detected on red blood cells (RBCs), the majority of the biochemical studies have been performed on Lewis substances isolated from plasma or saliva. There are four Lewis antigens, termed Lewis A (Lea), Lewis B (Leb), Lewis X (Lex) and Lewis Y (Ley).

ABO Blood Antigens

The discovery that the red blood cells (RBCs) of some people were agglutinated by soluble factors in the serum of other people led to the discovery of the ABO blood group system. The A, B, and H antigens are formed by the sequential action of glycosyltransferases which are encoded by four genes (the A, B, H, and Secretor [Se] genes). The blood group sugars are seeing increasing use beyond blood type laboratories in a wide variety of applications.

Aliphatic Bromoalkenes

 The bromine atom can be displaced by nucleophiles, act as a precursor to carbon centred radicals and participate in organometallic chemistry reactions via the formation of Grignard reagents, organozinc reagents or bromine-lithium exchange processes to yield organolithium reagents.

4,4'- and 6,6'-Substituted Bipyridines

2,2’-Bipyridine and its substituted analogues are of significant interest in coordination chemistry, due to their ability to act as bidentate chelating ligands, forming complexes with a range of transition metals. 

3-Alkyl Thiophenes

Research into organic semiconducting materials has grown significantly, and semiconductivity has been shown by single molecules, oligomers and organic polymers, such as those resulting from polymerisation of 3-alkylthiophenes supplied by Carbosynth.

LacNAc in Cell Biology and Synthetic Research

N-Acetyl-D-lactosamine (LacNAc) is a disaccharide containing galactose and N-acetylglucose units. LacNAc and derivatives are widely used in the characterization and investigation of lectins. LacNAc is an essential component of the tetrasaccharide Sialyl LewisX that are found on the surfaces of leukocytes. LacNAc is also used for investigating the roles of galactosidase, fucosyltransferase and sialyltransferase enzymes.

X-Gal for β-Galactosidase Assays

5-Bromo-4-chloro-3-indolyl β-D-galactopyranoside (X-Gal) is frequently used in molecular biology to indicate the activity of β-galactosidase, an enzyme encoded by the lacZ gene. X-Gal is enzymatically hydrolysed by β-galactosidase to yield galactose and 5-bromo-4-chloro-3-hydroxyindole. The soluble, colourless, product is subsequently transformed into an insoluble blue compound, 5,5’-dibromo-4,4’-dichloro indigo.

TEMPO in Catalytic and Oxidation Processes

2,2,6,6-Tetramethylpiperidine 1-oxyl (TEMPO) is a remarkably stable nitroxyl radical. It is frequently used in organic synthesis as a catalytic oxidant. TEMPO is also used in the oxidation of alcohol, amines, phosphines, phenols, anilines, sulfides and organometallic compounds.

Multiple Applications of 2-Deoxy-D-Ribose

The phosphorylated variants of 2-Deoxy-D-ribose (nucleotides) are important units constituting the DNA. 2-Deoxy-D-ribose has also been used as an intermediate for synthesising an antiviral nucleoside, called North-methanocarbathymidine (N-MCT). The natural products (-)-brevenal and ent-obtusenyne can also be synthesized from 2-Deoxy-D-ribose.

(R)- or (S)-3-Quinuclidinol in Ligands of Muscarinic Receptors

Muscarinic receptors are G protein-coupled acetylcholine receptors found in the plasma membranes of certain neurons and other cells that are involved in diverse physiological functions such as smooth muscle contraction, exocrine and endocrine secretion, and nerve-to-nerve transmission. Quinuclidinol derived molecules include talsaclidine and revatropate.

Cyanogen Bromide in Organic Synthesis and as a Coupling Reagent

Cyanogen bromide has many uses in synthetic organic chemistry.  It has been used for the synthesis of guanidines, hydroxyguanidines, heterocyclic systems, ureas and thioureas. In biochemistry, cyanogen bromide is frequently used to immobilize proteins for affinity chromatography, by coupling them to reagents such as agarose. Cyanogen bromide is also a convenient reagent for the synthesis of amino-heterocycles.

Carbohydrate-Based Detergents

The carbohydrate-based detergents, offered by Carbosynth, are classed as non-ionic, as their hydrophilic head groups are not charged (ionised). Non-ionic detergents are typically mild solubilizing and dissociating agents used in the solubilization and purification of integral membrane proteins, and frequently allow the retention of the native structure and function of the protein. Additional diverse uses include in agriculture, oil recovery applications and the cosmetics industry.

Diphenylcyclopropenone in Synthetic Chemistry and Medicine

Outside the field of synthetic chemistry, diphenylcyclopropenone finds utility in medicine, where it is often referred to as diphencyprone. Applied topically, diphenylcyclopropenone is used as a treatment for cutaneous warts, atopic dermatitis and alopecia areata. Recently it has shown use in cutaneous metastatic melanoma, in combination chemotherapy and radiotherapy. 

EDAC as a Modern Coupling Agent and its Other Uses

EDAC, also known as water-soluble carbodiimide, is a versatile modern coupling agent that is used for the synthesis of pharmaceuticals. EDAC has also been applied in combinatorial chemistry to attach carboxylic acids to a poly amine support and for the preparation of bio-sensors. Other uses include in photographic films and prosthetic implants.

IPTG as an Inducer of the Lac Operon-Based Expression Systems

IPTG is used as a molecular mimic of allolactose, a lactose metabolite that promotes transcription of the lac operon. It binds to the lac repressor, freeing the lac operon for transcription. IPTG is advantageous for in vivo studies as, unlike allolactose, the sulfur linkage is non-hydrolyzable by E. coli. X-Gal and IPTG are used in combination in agar media to identify bacterial colonies with a functional lacZ gene.

L-Sorbose as Precursor of Rare Sugars

L-Sorbose belongs to the L-series of natural sugars that has a sweetness equivalent to sucrose. It is produced from D-Sorbitol by Gluconobacter oxydans or Acetobacter species, via regiocontrolled dehydrogenation. L-sorbose is also used as a precursor for the synthesis of other rare sugars such as L-tagatose and L-iditol. L-Sorbose has also been applied to microbial culture media, where it has been observed to alter the growth rate of fungi.

MUG, a Fluorogenic Substrate for β-Glucuronidase

4-Methylumbelliferyl β-D-glucuronide dihydrate (MUG) is a fluorogenic substrate for β-glucuronidase. A common use for MUG is as a substrate for β-glucuronidase in the GUS reporter gene system. β-Glucuronidase is encoded by GUS and is frequently used as a marker gene in transgenic plants.

PUGNAc, an Inhibitor of O-Linked Protein Glycosylation

O-(2-Acetamido-2-deoxy-D-glucopyranosylidene) amino N-phenyl carbamate (PUGNAc) is a potent inhibitor of the enzyme O-GlcNAcase. PUGNAc is also an inhibitor of the functionally-related enzyme β-hexosaminidase. It has been shown to provide a protective effect on cardiac function after trauma-haemorrhage in rodents.

Role of Sialic Acid in Biology and Synthetic Carbohydrate Chemistry

N-Acetylneuraminic acid (sialic acid) is widely distributed in human tissues and is found in glycoproteins on cell membranes and in glycolipids such as gangliosides. It is involved in diverse biological functions including neurotransmission, leukocyte extravasation, viral or bacterial infections and carbohydrate-protein recognition events leading to cell adhesion. 

CNPF Hydrolysis in Assays for Diagnosis of Hepatocellular Carcinoma

2-Chloro-4-nitrophenyl α-L-fucopyranoside (CNPF) is a substrate for the enzyme α-L-fucosidase (AFU). The levels of AFU in human serum are useful markers for diagnosing hepatocellular carcinoma (HCC). A highly sensitive and specific assay monitoring the hydrolysis of CNPF by AFU has been developed, for use in the early diagnosis of HCC. This assay can be accommodated for automated clinical analyzers for large-scale screening purposes.

2’-C-Methyl Ribonucleosides as Antiviral Pro-Drugs

2’-C-Methyl ribonucleosides are sugar-modified ribonucleoside analogues, possessing a beta-alkyl substituent at the 2’ position of the ribose moiety. These inhibit replication of HCV and Flaviviridae viruses. Therapeutic use is limited by poor pharmacokinetic parameters, which has been overcome by the development of pro-drugs such as Valopicitabine and IDX-184.

ONPG for β-Galactosidase Assays

Also known as 2-nitrophenyl β-D-galactopyranoside, this compound is used in colourimetric and spectrophotometric assays for the detection of β-galactosidase activity which is of interest in clinical, food, environmental, and molecular biology arenas. ONPG is hydrolysed by β-galactosidase to yield galactose and ortho-nitrophenol, which absorbs light at 420 nm and can be used for spectrophotometric measurements.

Glycosidase Enzyme Substrates

Enzyme substrates are reagents used for testing or measuring enzyme activity. The appropriate glycoside hydrolase enzyme cleaves the glycosidic bond releasing the sugar and a chromogenic or fluorogenic marker. Carbosynth offers four main classes of glycosidase substrates: indolyl (for e.g. X-Gal), nitrophenyl (for e.g. ONPG), methylumbelliferyl (for e.g. MUG) and phosphates (for e.g. magenta phosphate). 

A HOBt Replacement: HOPO

A recent change in the UN classification of HOBt resulting in more restrictive shipping regulations has led to interest in the lesser known alternative, 2-hydroxypyridine-N-oxide (HOPO). The major use for HOPO is in amide bond synthesis. Use of this compound is not only limited to organic synthesis but it is also studied in disorders involving iron imbalance and for understanding the mechanism of iron chelators. 

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