Anticapsin
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-00551 |
| CAS | 28978-07-6 |
| Molecular Weight | 199.20 |
| Molecular Formula | C9H13NO4 |
Online Inquiry
Description
Anticapsin is an antibiotic produced by Streptomyces griseoplanus. It can also be produced by acid hydrolysis of Bacilysin. 3 μg/mL Anticapsin can inhibit the formation of hyaluronic acid capsule by Streptococcus pyogenes. Except for Salmonella gallisepticum (MIC 6.25 μg/mL), low concentration has no obvious antibacterial activity against other microorganisms.
Specification
| Synonyms | 7-Oxabicyclo[4.1.0]heptane-2-propanoic acid, (1R-(1.alpha.,2.alpha.(S*),6.alpha.))- |
| IUPAC Name | (2S)-2-amino-3-[(1R,2R,6R)-5-oxo-7-oxabicyclo[4.1.0]heptan-2-yl]propanoic acid |
| Canonical SMILES | C1CC(=O)C2C(C1CC(C(=O)O)N)O2 |
| InChI | InChI=1S/C9H13NO4/c10-5(9(12)13)3-4-1-2-6(11)8-7(4)14-8/h4-5,7-8H,1-3,10H2,(H,12,13)/t4-,5+,7-,8+/m1/s1 |
| InChI Key | KHVZXXWDPSCGEK-ROHCDXGRSA-N |
Properties
| Appearance | White Crystals |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 415.9°C at 760 mmHg |
| Melting Point | 240°C (dec.) |
| Density | 1.368 g/cm3 |
| Solubility | Soluble in Water, Methanol |
Reference Reading
1. Investigation of anticapsin biosynthesis reveals a four-enzyme pathway to tetrahydrotyrosine in Bacillus subtilis
Sarah A Mahlstedt, Christopher T Walsh Biochemistry. 2010 Feb 9;49(5):912-23. doi: 10.1021/bi9021186.
Bacillus subtilis produces the antibiotic anticapsin as an L-Ala-L-anticapsin dipeptide precursor known as bacilysin, whose synthesis is encoded by the bacA-D genes and the adjacent ywfGH genes. To evaluate the biosynthesis of the epoxycyclohexanone amino acid anticapsin from the primary metabolite prephenate, we have overproduced, purified, and characterized the activity of the BacA, BacB, YwfH, and YwfG proteins. BacA is an unusual prephenate decarboxylase that avoids the typical aromatization of the cyclohexadienol ring by protonating C(8) to produce an isomerized structure. BacB then catalyzes an allylic isomerization, generating a conjugated dienone with a 295 nm chromophore. Both the BacA and BacB products are regioisomers of H(2)HPP (dihydro-4-hydroxyphenylpyruvate). The BacB product is then a substrate for the short chain reductase YwfH which catalyzes the conjugate addition of hydride at the C(4) olefinic terminus using NADH to yield the cyclohexenol-containing tetrahydro-4-hydroxyphenylpyruvate H(4)HPP. In turn, this keto acid is a substrate for YwfG, which promotes transamination (with L-Phe as amino donor), to form tetrahydrotyrosine (H(4)Tyr). Thus BacA, BacB, YwfH, and YwfG act in sequence in a four enzyme pathway to make H(4)Tyr, which has not previously been identified in B. subtilis but is a recognized building block in cyanobacterial nonribosomal peptides such as micropeptins and aeruginopeptins.
2. Molecular insights into the antifungal mechanism of bacilysin
Tao Wang, Xiao-Huan Liu, Mian-Bin Wu, Shun Ge J Mol Model. 2018 Apr 26;24(5):118. doi: 10.1007/s00894-018-3645-4.
Bacilysin is one of the simplest antimicrobial peptides and has drawn great attention for its excellent performance against Candida albicans. In this study, the antifungal mechanism of bacilysin was investigated. The target enzyme glucosamine-6-phosphate synthase (GFA) was expressed heterologously in Escherichia coli and its inhibition by bacilysin and derivatives was studied. It was concluded that bacilysin could be hydrolyzed by a proteinase of C. albicans, and that the released product, anticapsin, then inhibited the aminotransferase activity of GFA. This result was verified by molecular simulation, and the interaction mode of anticapsin with GFA was detailed, which provides data for the development of novel antifungal drugs. Transport of bacilysin into fungal cells was also simulated and it was shown that bacilysin is more readily transported into cells than anticapsin. Thus, our findings support a mechanism whereby bacilysin is transported into fungal pathogens, hydrolyzed to anticapsin, which then inhibits GFA.
3. Inhibition of glucosamine synthase by bacilysin and anticapsin
H Chmara J Gen Microbiol. 1985 Feb;131(2):265-71. doi: 10.1099/00221287-131-2-265.
L-Glutamine:D-fructose-6-phosphate amidotransferase ('glucosamine synthase', EC 5.3.1.19) from Escherichia coli MRE 600 was purified at least 75-fold. It catalysed the formation of 21.1 mumol glucosamine 6-phosphate (mg protein)-1 in 30 min at 37 degrees C. Its molecular weight, estimated by gel filtration, was about 90000 and it was inhibited by thiol group reagents. Anticapsin, the C-terminal amino acid of the dipeptide antibiotic bacilysin, and to a lesser extent bacilysin itself, inhibited glucosamine synthase activity. Kinetic studies indicated that the inhibition was non-competitive with respect to fructose 6-phosphate as substrate but partly competitive with respect to L-glutamine. Incubation of the enzyme with anticapsin brought about a time-dependent and irreversible inhibition. It is suggested that anticapsin behaves as a glutamine analogue and that a reaction of its epoxide group with a thiol group of glucosamine synthase results in its linkage to the enzyme by a covalent bond.
Recommended Products
| BBF-03754 | CASTANOSPERMINE | Inquiry |
| BBF-02642 | Lactonamycin | Inquiry |
| BBF-05862 | Epirubicin | Inquiry |
| BBF-01693 | Doxorubicin EP Impurity A (Daunorubicin) | Inquiry |
| BBF-01825 | Loganin | Inquiry |
| BBF-00677 | 3-Amino-3-deoxy-D-glucose | Inquiry |
Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
