Sch 642305

Last updated
Sch 642305
Sch 642305 Structure.svg
Names
Preferred IUPAC name
(4S,8aR,12S,12aR)-12-Hydroxy-4-methyl-4,5,6,7,8,8a,12,12a-octahydro-2H-3-benzoxecine-2,9(1H)-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C14H20O4/c1-9-4-2-3-5-10-11(8-14(17)18-9)13(16)7-6-12(10)15/h6-7,9-11,13,16H,2-5,8H2,1H3/t9-,10+,11+,13-/m0/s1
    Key: WTQWDNIIFGEBSZ-WGBDABJCSA-N)O
  • C[C@H]1CCCC[C@@H]2[C@@H](CC(=O)O1)[C@H](C=CC2=O)O
Properties
C14H20O4
Molar mass 252.310 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Sch 642305 is a chemical compound isolated from Penicillium verrucosum that inhibits bacterial DNA primase. [1]

Related Research Articles

DNA replication Biological process

In molecular biology, DNA replication is the biological process of producing two identical replicas of DNA from one original DNA molecule. DNA replication occurs in all living organisms acting as the most essential part for biological inheritance. This is essential for cell division during growth and repair of damaged tissues, while it also ensures that each of the new cells receives its own copy of the DNA. The cell possesses the distinctive property of division, which makes replication of DNA essential.

Polymerase

A polymerase is an enzyme that synthesizes long chains of polymers or nucleic acids. DNA polymerase and RNA polymerase are used to assemble DNA and RNA molecules, respectively, by copying a DNA template strand using base-pairing interactions or RNA by half ladder replication.

DNA primase is an enzyme involved in the replication of DNA and is a type of RNA polymerase. Primase catalyzes the synthesis of a short RNA segment called a primer complementary to a ssDNA template. After this elongation, the RNA piece is removed by a 5' to 3' exonuclease and refilled with DNA.

DnaG is a bacterial DNA primase and is encoded by the dnaG gene. The enzyme DnaG, and any other DNA primase, synthesizes short strands of RNA known as oligonucleotides during DNA replication. These oligonucleotides are known as primers because they act as a starting point for DNA synthesis. DnaG catalyzes the synthesis of oligonucleotides that are 10 to 60 nucleotides long, however most of the oligonucleotides synthesized are 11 nucleotides. These RNA oligonucleotides serve as primers, or starting points, for DNA synthesis by bacterial DNA polymerase III. DnaG is important in bacterial DNA replication because DNA polymerase cannot initiate the synthesis of a DNA strand, but can only add nucleotides to a preexisting strand. DnaG synthesizes a single RNA primer at the origin of replication. This primer serves to prime leading strand DNA synthesis. For the other parental strand, the lagging strand, DnaG synthesizes an RNA primer every few kilobases (kb). These primers serve as substrates for the synthesis of Okazaki fragments.

Pre-replication complex

A pre-replication complex (pre-RC) is a protein complex that forms at the origin of replication during the initiation step of DNA replication. Formation of the pre-RC is required for DNA replication to occur. Complete and faithful replication of the genome ensures that each daughter cell will carry the same genetic information as the parent cell. Accordingly, formation of the pre-RC is a very important part of the cell cycle.

Filamentation

Filamentation is the anomalous growth of certain bacteria, such as Escherichia coli, in which cells continue to elongate but do not divide. The cells that result from elongation without division have multiple chromosomal copies. In the absence of antibiotics or other stressors, filamentation occurs at a low frequency in bacterial populations, the increased cell length protecting bacteria from protozoan predation and neutrophil phagocytosis by making ingestion of the cells more difficult. Filamentation is also thought to protect bacteria from antibiotics, and is associated with other aspects of bacterial virulence such as biofilm formation. The number and length of filaments within a bacterial population increases when the bacteria are treated with various chemical and physical agents. Some of the key genes involved in filamentation in E. coli include sulA and minCD.

Type II topoisomerase

Type II topoisomerases are topoisomerases that cut both strands of the DNA helix simultaneously in order to manage DNA tangles and supercoils. They use the hydrolysis of ATP, unlike Type I topoisomerase. In this process, these enzymes change the linking number of circular DNA by ±2.

Prokaryotic DNA replication

Prokaryotic DNA Replication is the process by which a prokaryote duplicates its DNA into another copy that is passed on to daughter cells. Although it is often studied in the model organism E. coli, other bacteria show many similarities. Replication is bi-directional and originates at a single origin of replication (OriC). It consists of three steps: Initiation, elongation, and termination.

MCM3AP

80 kDa MCM3-associated protein is a protein that in humans is encoded by the MCM3AP gene.

PRIM2

DNA primase large subunit is an enzyme that in humans is encoded by the PRIM2 gene.

Purine analogues are antimetabolites that mimic the structure of metabolic purines.

Mark Griep is a chemistry professor at the University of Nebraska-Lincoln. He has a bachelor’s and doctorate in biochemistry from the University of Minnesota. He studies the enzymes primase and DnaB helicase in his search for antibiotics that inhibit them. He is co-author with Marjorie Mikasen of the nonfiction book ReAction! Chemistry in the Movies.

Circular chromosome

A circular chromosome is a chromosome in bacteria, archaea, mitochondria, and chloroplasts, in the form of a molecule of circular DNA, unlike the linear chromosome of most eukaryotes.

PrimPol

PrimPol is a protein encoded by the PRIMPOL gene in humans. PrimPol is a eukaryotic protein with both DNA polymerase and DNA Primase activities involved in translesion DNA synthesis. It is the first eukaryotic protein to be identified with priming activity using deoxyribonucleotides. It is also the first protein identified in the mitochondria to have translesion DNA synthesis activities.

Single-stranded binding protein

Single-stranded binding proteins (SSBs) are a class of proteins that have been identified in both viruses and organisms from bacteria to humans.

PRIM1

DNA primase small subunit is an enzyme that in humans is encoded by the PRIM1 gene.

DNA polymerase alpha catalytic subunit

DNA polymerase alpha catalytic subunit is an enzyme that in humans is encoded by the POLA1 gene.

DNA polymerase alpha

DNA polymerase alpha also known as Pol α is an enzyme complex found in eukaryotes that is involved in initiation of DNA replication. The DNA polymerase alpha complex consists of 4 subunits: POLA1, POLA2, PRIM1, and PRIM2.

A helicase–primase complex is a complex of enzymes including DNA helicase and DNA primase. A helicase-primase associated factor protein may also be present.

Amenamevir

Amenamevir is an antiviral drug used for the treatment of shingles.

References

  1. Chu, Min; Mierzwa, Ronald; Xu, Ling; He, Ling; Terracciano, Joseph; Patel, Mahesh; Gullo, Vincent; Black, Todd; Zhao, Wenjun; Chan, Tze-Ming; McPhail, Andrew T (2003). "Isolation and Structure Elucidation of Sch 642305, a Novel Bacterial DNA Primase Inhibitor Produced by Penicilliumverrucosum". Journal of Natural Products. 66 (12): 1527–30. doi:10.1021/np0302302. PMID   14695789.