A heptose is a

monosaccharide Monosaccharides (from Greek '' monos'': single, '' sacchar'': sugar), also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built. Chemically, monosaccharides are polyhy ...

with seven

carbon Carbon () is a chemical element; it has chemical symbol, symbol C and atomic number 6. It is nonmetallic and tetravalence, tetravalent—meaning that its atoms are able to form up to four covalent bonds due to its valence shell exhibiting 4 ...

atoms. They have either an

aldehyde In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...

functional group In organic chemistry, a functional group is any substituent or moiety (chemistry), moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions r ...

in position 1 (aldoheptoses) or a

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

functional group in position 2, 3 or 4 (ketoheptoses). Ketoheptoses have 4 chiral centers, whereas aldoheptoses have 5.

Examples

There are few examples of seven-carbon sugars in nature, among which are: * sedoheptulose or D-''altro''-heptulose (a ketose), an intermediate in the

Calvin cycle The Calvin cycle, light-independent reactions, bio synthetic phase, dark reactions, or photosynthetic carbon reduction (PCR) cycle of photosynthesis is a series of chemical reactions that convert carbon dioxide and hydrogen-carrier compounds into ...

and in

lipid A Lipid A is a lipid component of an endotoxin held responsible for the toxicity of gram-negative bacteria. It is the innermost of the three regions of the lipopolysaccharide (LPS), also called endotoxin molecule, and its hydrophobic nature allows ...

biosynthesis * mannoheptulose (a ketose), found in

avocado The avocado, alligator pear or avocado pear (''Persea americana'') is an evergreen tree in the laurel family (Lauraceae). It is native to Americas, the Americas and was first domesticated in Mesoamerica more than 5,000 years ago. It was priz ...

es * L-''glycero''-D-''manno''-heptose (an aldose), a late intermediate in lipid A biosynthesis.

Structural role

The production of heptose is conserved across

gram-negative bacteria Gram-negative bacteria are bacteria that, unlike gram-positive bacteria, do not retain the Crystal violet, crystal violet stain used in the Gram staining method of bacterial differentiation. Their defining characteristic is that their cell envelo ...

. In the form of L-glycero-D-mannose-heptose, heptose is a key component in the secondary membrane of gram-negative bacteria. Gram-negative bacteria, in addition to having a

cell wall A cell wall is a structural layer that surrounds some Cell type, cell types, found immediately outside the cell membrane. It can be tough, flexible, and sometimes rigid. Primarily, it provides the cell with structural support, shape, protection, ...

, are also encapsulated by a membrane composed of lipopolysaccharides. These lipopolysaccharides comprise an

endotoxin Lipopolysaccharide (LPS), now more commonly known as endotoxin, is a collective term for components of the outermost membrane of the cell envelope of gram-negative bacteria, such as '' E. coli'' and ''Salmonella'' with a common structural archit ...

that acts as an immune system

agonist An agonist is a chemical that activates a Receptor (biochemistry), receptor to produce a biological response. Receptors are Cell (biology), cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an R ...

and elicits strong responses. This toxin, known as

, consists of a core of one to three heptose molecules. The 7-carbon heptose molecules are essential for stability in the lipopolysaccharide membrane, forming an interconnected network utilizing divalent cations.

Role in cell signaling

Heptose, in the form of heptose 1-7-bisphosphate, has been found to be one of the components responsible for the

pathogenic In biology, a pathogen (, "suffering", "passion" and , "producer of"), in the oldest and broadest sense, is any organism or agent that can produce disease. A pathogen may also be referred to as an infectious agent, or simply a germ. The term ...

nature of gram negative bacteria. In the bacterium biosynthesis pathway, heptose is

phosphorylated In biochemistry, phosphorylation is described as the "transfer of a phosphate group" from a donor to an acceptor. A common phosphorylating agent (phosphate donor) is ATP and a common family of acceptor are alcohols: : This equation can be writt ...

to heptose 1-7-bisphosphate. In addition, like other sugars, heptose may exist in either the alpha anomer or the beta anomer. Before synthetic production of heptose-bisphosphate (HBP) for studies, cytosolic HBP was thought to influence NF-kB, a

transcription factor In molecular biology, a transcription factor (TF) (or sequence-specific DNA-binding factor) is a protein that controls the rate of transcription (genetics), transcription of genetics, genetic information from DNA to messenger RNA, by binding t ...

in mammalian cells. Along with producing the first synthetic version of HBP, it was shown that the beta form of the heptose acts as a

pathogen-associated molecular pattern Pathogen-associated molecular patterns (PAMPs) are small molecular motifs conserved within a class of microbes, but not present in the host. They are recognized by toll-like receptors (TLRs) and other pattern recognition receptors (PRRs) in both p ...

(PAMP) and activates the NF-kB signaling pathway. A PAMP is a specific structure, component, or molecule that triggers the immune response after recognition by pattern recognition receptors on mammalian cells.

References

{{Carbohydrates