![]() | This article may be too technical for most readers to understand.(June 2017) |
![]() | |
Names | |
---|---|
Other names
Jadomycin L-isoleucine
| |
Identifiers | |
| |
3D model (
JSmol)
|
|
ChEBI |
|
ChEMBL | |
ChemSpider | |
KEGG | |
PubChem
CID
|
|
| |
| |
Properties | |
C30H31NO9 | |
Molar mass | 549.576 g·mol−1 |
Appearance | Deep red-purple solid |
Solubility | Soluble in various organic solvents[ vague] |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
A jadomycin is a natural product produced by Streptomyces venezuelae ISP5230 (ATCC10712 [1]), the organism which is most well known for making the antibiotic chloramphenicol. The name jadomycin is applied to a family of related angucyclines which are distinguished by the E ring (usually an oxoazolone ring), which is derived from an amino acid. The amino acid incorporation which forms the E-ring is a chemical reaction, rather than enzymatic, an uncommon occurrence in biosynthesis. As such a number of jadomycins incorporating different amino acids have been discovered. Jadomycin A was the first compound of this family to be isolated and constitutes the angucylic backbone with L-isoleucine incorporated into the E-ring. [2] A related analog, jadomycin B, is modified by glycosylation with a 2,6-dideoxy sugar, L-digitoxose. [3] Jadomycins have cytotoxic and antibacterial properties.
The jadomycin biosynthetic gene cluster is well characterized. Jadomycin biosynthesis encompasses type II polyketide synthase (T2Pks) assembly to generate the angucycline component, [4] and a dideoxy sugar pathway, to generate the sugar donor NDP-L-digitoxose. [5] Studies have implicated JadG, an FAD-dependent oxygenase, in the ring cleavage required for incorporation of amino acids. [6] JadS, the glycosyltransferase that transfers L-digitoxose, has been shown to be flexible with respect to the sugar donor. [7] [8] [9]
Jadomycin analogs have been obtained through culture of S. venezuelae in the presence of a single amino acid. The diversity of jadomycins includes those incorporating naturally occurring amino acids, [10] non-proteinogenic amino acids, [11] [12] and synthetic amino acids with handles enabling further chemical modification. [13] [14]
![]() | This article may be too technical for most readers to understand.(June 2017) |
![]() | |
Names | |
---|---|
Other names
Jadomycin L-isoleucine
| |
Identifiers | |
| |
3D model (
JSmol)
|
|
ChEBI |
|
ChEMBL | |
ChemSpider | |
KEGG | |
PubChem
CID
|
|
| |
| |
Properties | |
C30H31NO9 | |
Molar mass | 549.576 g·mol−1 |
Appearance | Deep red-purple solid |
Solubility | Soluble in various organic solvents[ vague] |
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
A jadomycin is a natural product produced by Streptomyces venezuelae ISP5230 (ATCC10712 [1]), the organism which is most well known for making the antibiotic chloramphenicol. The name jadomycin is applied to a family of related angucyclines which are distinguished by the E ring (usually an oxoazolone ring), which is derived from an amino acid. The amino acid incorporation which forms the E-ring is a chemical reaction, rather than enzymatic, an uncommon occurrence in biosynthesis. As such a number of jadomycins incorporating different amino acids have been discovered. Jadomycin A was the first compound of this family to be isolated and constitutes the angucylic backbone with L-isoleucine incorporated into the E-ring. [2] A related analog, jadomycin B, is modified by glycosylation with a 2,6-dideoxy sugar, L-digitoxose. [3] Jadomycins have cytotoxic and antibacterial properties.
The jadomycin biosynthetic gene cluster is well characterized. Jadomycin biosynthesis encompasses type II polyketide synthase (T2Pks) assembly to generate the angucycline component, [4] and a dideoxy sugar pathway, to generate the sugar donor NDP-L-digitoxose. [5] Studies have implicated JadG, an FAD-dependent oxygenase, in the ring cleavage required for incorporation of amino acids. [6] JadS, the glycosyltransferase that transfers L-digitoxose, has been shown to be flexible with respect to the sugar donor. [7] [8] [9]
Jadomycin analogs have been obtained through culture of S. venezuelae in the presence of a single amino acid. The diversity of jadomycins includes those incorporating naturally occurring amino acids, [10] non-proteinogenic amino acids, [11] [12] and synthetic amino acids with handles enabling further chemical modification. [13] [14]