Synonym
Rhizocticin A; Arg-appa;
IUPAC/Chemical Name
(S,Z)-2-((S)-2-amino-5-guanidinopentanamido)-5-phosphonopent-3-enoic acid
InChi Key
BLNRPHBKOMCMBX-ABXVWLFBSA-N
InChi Code
InChI=1S/C11H22N5O6P/c12-7(3-1-5-15-11(13)14)9(17)16-8(10(18)19)4-2-6-23(20,21)22/h2,4,7-8H,1,3,5-6,12H2,(H,16,17)(H,18,19)(H4,13,14,15)(H2,20,21,22)/b4-2-/t7-,8-/m0/s1
SMILES Code
O=C(O)[C@H](/C=C\CP(O)(O)=O)NC([C@H](CCCNC(N)=N)N)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Preparing Stock Solutions
The following data is based on the
product
molecular weight
351.29
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Gahungu M, Arguelles-Arias A, Fickers P, Zervosen A, Joris B, Damblon C, Luxen A. Synthesis and biological evaluation of potential threonine synthase inhibitors: Rhizocticin A and Plumbemycin A. Bioorg Med Chem. 2013 Sep 1;21(17):4958-67. doi: 10.1016/j.bmc.2013.06.064. Epub 2013 Jul 8. PubMed PMID: 23891162.
2: Kugler M, Loeffler W, Rapp C, Kern A, Jung G. Rhizocticin A, an antifungal phosphono-oligopeptide of Bacillus subtilis ATCC 6633: biological properties. Arch Microbiol. 1990;153(3):276-81. PubMed PMID: 2110446.
3: Kino K, Kotanaka Y, Arai T, Yagasaki M. A novel L-amino acid ligase from Bacillus subtilis NBRC3134, a microorganism producing peptide-antibiotic rhizocticin. Biosci Biotechnol Biochem. 2009 Apr 23;73(4):901-7. Epub 2009 Apr 7. PubMed PMID: 19352016.
4: Kino K. [Novel L-amino acid ligases catalyzing oligopeptide synthesis]. Yakugaku Zasshi. 2010 Nov;130(11):1463-9. Review. Japanese. PubMed PMID: 21048404.
5: Fredenhagen A, Angst C, Peter HH. Digestion of rhizocticins to (Z)-L-2-amino-5-phosphono-3-pentenoic acid: revision of the absolute configuration of plumbemycins A and B. J Antibiot (Tokyo). 1995 Sep;48(9):1043-5. PubMed PMID: 7592051.
6: Bareich DC, Nazi I, Wright GD. Simultaneous in vitro assay of the first four enzymes in the fungal aspartate pathway identifies a new class of aspartate kinase inhibitor. Chem Biol. 2003 Oct;10(10):967-73. PubMed PMID: 14583263.
