Pyloricidin D
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| Category | Antibiotics |
| Catalog number | BBF-02084 |
| CAS | |
| Molecular Weight | 342.34 |
| Molecular Formula | C15H22N2O7 |
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Description
Pyloricidin D is an antibiotic against Helicobacter pylori produced by Bacillus sp. HC-70.
Specification
| IUPAC Name | (3R)-3-[[(2R,3S,4S,5R)-5-amino-2,3,4,6-tetrahydroxyhexanoyl]amino]-3-phenylpropanoic acid |
| Canonical SMILES | C1=CC=C(C=C1)C(CC(=O)O)NC(=O)C(C(C(C(CO)N)O)O)O |
| InChI | InChI=1S/C15H22N2O7/c16-9(7-18)12(21)13(22)14(23)15(24)17-10(6-11(19)20)8-4-2-1-3-5-8/h1-5,9-10,12-14,18,21-23H,6-7,16H2,(H,17,24)(H,19,20)/t9-,10-,12+,13+,14-/m1/s1 |
| InChI Key | GVOBXKQKXYPNTR-SJVBDLOYSA-N |
Properties
| Appearance | Colorless Needle Crystal |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Boiling Point | 788.9±60.0°C at 760 mmHg |
| Density | 1.5±0.1 g/cm3 |
Reference Reading
1. Synthesis and anti-Helicobacter pylori activity of pyloricidin derivatives I. Structure-activity relationships on the terminal peptidic moiety
Atsushi Hasuoka, Yuji Nishikimi, Yutaka Nakayama, Keiji Kamiyama, Masafumi Nakao, Ken-ichiro Miyagawa, Osamu Nishimura, Masahiko Fujino J Antibiot (Tokyo). 2002 Mar;55(3):322-36. doi: 10.7164/antibiotics.55.322.
The novel natural antibiotics pyloricidin A, B and C possess potent and highly selective antibacterial activity against Helicobacter pylori. In order to investigate the structure activity relationships for the terminal peptidic moiety, a series of pyloricidin B and pyloricidin C derivatives, bearing various amino acids in the moiety, were prepared and evaluated for their anti-H. pylori activity. The derivatives bearing alpha-D-, beta- and gamma-amino acids or peptidemimetics showed drastically decreased activity. On the other hand, the derivatives with a-L-amino acids were found to maintain the activity. Among the derivatives prepared in this work, the allylglycine derivative 2s showed the most potent anti-H. pylori activity, with an MIC value of less than 0.006 microg/ml against H. pylori NCTC11637, which is 60-fold greater than the activity of the lead compound pyloricidin C.
2. Total synthesis of novel antibiotics pyloricidin A, B and C and their application in the study of pyloricidin derivatives
Atsushi Hasuoka, Yuji Nishikimi, Yutaka Nakayama, Keiji Kamiyama, Masafumi Nakao, Ken-ichiro Miyagawa, Osamu Nishimura, Masahiko Fujino J Antibiot (Tokyo). 2002 Feb;55(2):191-203. doi: 10.7164/antibiotics.55.191.
The novel natural antibiotics pyloricidin A, B and C, which possess potent and highly selective anti-Helicobacter pylori activity, were synthesized from D-galactosamine as a chiral template for the common (2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoic acid moiety. The synthetic strategy, using 2-amino-2-deoxyuronic acid derivatives as key intermediates, was also useful to prepare a series of derivatives modified at the beta-D-phenylalanine and with altered stereochemistry on the 5-amino-2,3,4,6-tetrahydroxyhexanoic acid moiety. From the drastic decrease of their anti-H. pylori activity, it was clear that the beta-D-phenylalanine part and the stereochemistry of the 5-amino-2,3,4,6-tetrahydroxyhexanoic acid moiety were significant for the activity.
3. Synthesis and anti-Helicobacter pylori activity of pyloricidin derivatives II. The combination of amino acid residues in the dipeptidic moiety and its effect on the anti-Helicobacter pylori activity
Atsushi Hasuoka, Yuji Nishikimi, Yutaka Nakayama, Keiji Kamiyama, Masafumi Nakao, Ken-ichiro Miyagawa, Osamu Nishimura, Masahiko Fujino J Antibiot (Tokyo). 2002 May;55(5):499-507. doi: 10.7164/antibiotics.55.499.
The novel natural antibiotics pyloricidin A, B and C, consisting of a common (2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl-beta-D-phenylalanine moiety and a terminal peptidic moiety (pyloricidin A: L-valine-L-valine-L-leucine; pyloricidin B: L-valine-L-leucine; pyloricidin C: L-leucine), exhibit potent and highly selective anti-Helicobacter pylori activity. In order to develop more potent compounds and to investigate structure activity relationships for the peptidic moiety with regard to the combination of amino acids, a series of derivatives with various dipeptidic moieties were prepared and evaluated for their anti-H. pylori activity. The combination of the two amino acids in the moiety was found to have a significant effect on the activity; the compound with Nva-Abu showed excellent anti-H. pylori activity with an MIC value of 0.013 microg/ml against H. pylori TN2. In addition, this compound was found to show 60% clearance of H. pylori from infected Mongolian gerbils upon repetitive oral administration (10 mg/kg, b. i. d. for 7 days).
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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 ╳
