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Prodiginines
The prodiginines are a family of red tripyrrole dyestuffs produced by Gammaproteobacteria (e.g. ''Serratia marcescens'') as well as some Actinomycetota (e.g. ''Streptomyces coelicolor''). The group is named after prodigiosin (prodiginine) and is biosynthesized through a common set of enzymes. They are interesting due to their history and their varied biological activity. Structural types Prodigiosin colour.svg, Prodigiosin Cycloprodigiosin.svg, Cycloprodigiosin Cyclononylprodigiosin.svg, Cyclononylprodigiosin Undecylprodigiosin coloured.svg, Undecylprodigiosin Butyl-meta-cycloheptylprodiginine.svg, Butyl-meta-cycloheptylprodiginine Natural sources The prodiginines are secondary metabolites originally noted in ''Serratia'' species, especially ''Serratia marcescens''. They are also found in Actinomycetes, for example ''Streptomyces coelicolor'' and some marine bacteria, including ''Hahella chejuensis'' and ''Pseudoalteromonas denitrificans''. Cyclononylprodigiosin was isolated f ...
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Prodigiosin
Prodigiosin is the red dyestuff produced by many strains of the bacterium ''Serratia marcescens'', as well as other Gram-negative, gamma proteobacteria such as ''Vibrio psychroerythrus'' and ''Hahella chejuensis''. It is responsible for the pink tint occasionally found in grime that accumulates on porcelain surfaces such as bathtubs, sinks, and toilet bowls. It is in the prodiginines family of compounds which are produced in some Gram-negative gamma proteobacteria, as well as select Gram-positive Actinobacteria (e.g. ''Streptomyces coelicolor''). The name ''prodigiosin'' is derived from ''prodigious'' (''i.e.'' something marvelous). Secondary metabolite Prodigiosin is a secondary metabolite of ''Serratia marcescens''. Because it is easy to detect, it has been used as a model system to study secondary metabolism. Prodigiosin production has long been known to be enhanced by phosphate limitation. In low phosphate conditions, pigmented strains have been shown to grow to a higher ...
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Undecylprodigiosin
Undecylprodigiosin is an alkaloid produced by some Actinomycetes bacteria. It is a member of the prodiginines group of natural products and has been investigated for potential antimalarial activity. Natural sources Undecylprodigiosin is a secondary metabolite found in some Actinomycetes, for example ''Actinomadura madurae'', ''Streptomyces coelicolor'' and '' Streptomyces longisporus''. Production Biosynthesis The biosynthesis of undecylprodigiosin starts with PCP apoprotein which is transformed into the holoprotein using acetyl CoA and PPtase then adenylation occurs utilizing L-proline and ATP. The resulting molecule is then oxidized by dehydrogenase enzyme. Elongation by decarboxylative condensation with malonyl CoA is followed by another decarboxylative condensation with L-serine using α-oxamine synthase (OAS) domain. The compound is then cyclized, oxidized with dehydrogenase and methylated with SAM to give 4-methoxy-2,2′-bipyrrole-5-carboxaldehyde (MBC) intermediat ...
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Serratia Marcescens
''Serratia marcescens'' () is a species of rod-shaped, Gram-negative bacteria in the family Yersiniaceae. It is a facultative anaerobe and an opportunistic pathogen in humans. It was discovered in 1819 by Bartolomeo Bizio in Padua, Italy.Serratia marcescens. (2011, April). Retrieved from https://microbewiki.kenyon.edu/index.php/Serratia_marcescens ''S. marcescens'' is commonly involved in hospital-acquired infections (HAIs), also called nosocomial infections, particularly catheter-associated bacteremia, urinary tract infections, and wound infections, and is responsible for 1.4% of HAI cases in the United States. It is commonly found in the respiratory and urinary tracts of hospitalized adults and in the gastrointestinal systems of children. Due to its abundant presence in the environment, and its preference for damp conditions, ''S. marcescens'' is commonly found growing in bathrooms (especially on tile grout, shower corners, toilet water lines, and basins), where it ...
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Bloody Bread - Serratia Marcescens In Action
''Bloody'', as an adjective or adverb, is a commonly used expletive attributive in British English, Australian English, Irish English, Indian English and a number of other Commonwealth nations. It has been used as an intensive since at least the 1670s. Considered respectable until about 1750, it was heavily tabooed during c. 1750–1920, considered equivalent to heavily obscene or profane speech. Public use continued to be seen as controversial until the 1960s, but since then, the word has become a comparatively mild expletive or intensifier. In American English, the word is used almost exclusively in its literal sense and is seen by American audiences as a stereotypical marker of British English, without any significant obscene or profane connotation. Canadian English usage is similar to American English, but use as an expletive adverb may be considered slightly vulgar depending on the circumstances. Origin Use of the adjective ''bloody'' as a profane intensifier p ...
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Actinomadura
The genus ''Actinomadura'' is one of four genera of Actinomycetota that belong to the family Thermomonosporaceae. It contains aerobic, Gram-positive, non-acid-fast, non-motile, chemo-organotrophic actinomycetes that produce well-developed, non-fragmenting vegetative mycelia and aerial hyphae that differentiate into surface-ornamented spore chains. These chains are of various lengths and can be straight, hooked or spiral. The genus currently comprises over 70 species with validly published names with standing in nomenclature, although the species status of some strains remains uncertain, and further comparative studies are needed. Members of the genus are not characterized chemotaxonomically by type III/B cell walls (meso-diaminopimelic acid and madurose are present) with peptidoglycan structures of the acetyl type. The predominant menaquinone types are MK-9(H4), MK-9(H6) and MK-9(H8). The phospholipid pattern is PI (diphosphatidylglycerol and phosphatidylinositol are present ...
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Pyrroles
Pyrrole is a heterocyclic aromatic organic compound, a five-membered ring with the formula C4 H4 NH. It is a colorless volatile liquid that darkens readily upon exposure to air. Substituted derivatives are also called pyrroles, e.g., ''N''-methylpyrrole, C4H4NCH3. Porphobilinogen, a trisubstituted pyrrole, is the biosynthetic precursor to many natural products such as heme. Pyrroles are components of more complex macrocycles, including the porphyrinogens and products derived therefrom, including porphyrins of heme, the chlorins, bacteriochlorins, and chlorophylls. Properties Pyrrole is a colorless volatile liquid that darkens readily upon exposure to air, and is usually purified by distillation immediately before use. Pyrrole has a nutty odor. Pyrrole is a 5-membered aromatic heterocycle, like furan and thiophene. Unlike furan and thiophene, it has a dipole in which the positive end lies on the side of the heteroatom, with a dipole moment of 1.58  D. In CDCl3, it has ...
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Total Synthesis
Total synthesis is the complete chemical synthesis of a complex molecule, often a natural product, from simple, commercially-available precursors. It usually refers to a process not involving the aid of biological processes, which distinguishes it from semisynthesis. Syntheses may sometimes conclude at a precursor with further known synthetic pathways to a target molecule, in which case it is known as a formal synthesis. Total synthesis target molecules can be natural products, medicinally-important active ingredients, known intermediates, or molecules of theoretical interest. Total synthesis targets can also be organometallic or inorganic, though these are rarely encountered. Total synthesis projects often require a wide diversity of reactions and reagents, and subsequently requires broad chemical knowledge and training to be successful. Often, the aim is to discover a new route of synthesis for a target molecule for which there already exist known routes. Sometimes, however, no ...
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Condensation Reaction
In organic chemistry, a condensation reaction is a type of chemical reaction in which two molecules are combined to form a single molecule, usually with the loss of a small molecule such as water. If water is lost, the reaction is also known as a dehydration synthesis. However other molecules can also be lost, such as ammonia, ethanol, acetic acid and hydrogen sulfide. The addition of the two molecules typically proceeds in a step-wise fashion to the addition product, usually in equilibrium, and with loss of a water molecule (hence the name condensation). The reaction may otherwise involve the functional groups of the molecule, and is a versatile class of reactions that can occur in acidic or basic conditions or in the presence of a catalyst. This class of reactions is a vital part of life as it is essential to the formation of peptide bonds between amino acids and to the biosynthesis of fatty acids. Many variations of condensation reactions exist. Common examples include the ...
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Aldehyde
In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are common and play important roles in the technology and biological spheres. Structure and bonding Aldehydes feature a carbon center that is connected by a double bond to oxygen and a single bond to hydrogen and single bond to a third substituent, which is carbon or, in the case of formaldehyde, hydrogen. The central carbon is often described as being sp2-Orbital hybridisation, hybridized. The aldehyde group is somewhat polar molecule, polar. The C=O bond length is about 120-122 picometers. Physical properties and characterization Aldehydes have properties that are diverse and that depend on the remainder of the molecule. Smaller aldehydes are more soluble in water, formaldehyde and acetaldehyde completely so. The volatile ...
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Serine
Serine (symbol Ser or S) is an α-amino acid that is used in the biosynthesis of proteins. It contains an α- amino group (which is in the protonated − form under biological conditions), a carboxyl group (which is in the deprotonated − form under biological conditions), and a side chain consisting of a hydroxymethyl group, classifying it as a polar amino acid. It can be synthesized in the human body under normal physiological circumstances, making it a nonessential amino acid. It is encoded by the codons UCU, UCC, UCA, UCG, AGU and AGC. Occurrence This compound is one of the naturally occurring proteinogenic amino acids. Only the L- stereoisomer appears naturally in proteins. It is not essential to the human diet, since it is synthesized in the body from other metabolites, including glycine. Serine was first obtained from silk protein, a particularly rich source, in 1865 by Emil Cramer. Its name is derived from the Latin for silk, ''sericum''. Serine's structure w ...
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