MedKoo Cat#: 597426 | Name: Phosalacine

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Phosalacine is a natural antimicrobial and herbicidal compound that has been isolated from the Actinobacteria Kitasatosporia phosalacinea. It is a tripeptide consisting of the amino acids glufosinate (phosphinothricin), alanine, and leucine. It is similar in structure to bialaphos, differing by replacement of the terminal alanine with leucine. Phosalacine has antimicrobial activity against Gram-positive and Gram-negative bacteria and some fungi. It also shows herbicidal activity against alfalfa It is believed that the herbicidal activity is due to the slow release of glufosinate, which is a commercially-used broad spectrum herbicide.

Chemical Structure

Phosalacine
Phosalacine
CAS#92567-89-0

Theoretical Analysis

MedKoo Cat#: 597426

Name: Phosalacine

CAS#: 92567-89-0

Chemical Formula: C14H28N3O6P

Exact Mass: 365.1716

Molecular Weight: 365.36

Elemental Analysis: C, 46.02; H, 7.72; N, 11.50; O, 26.27; P, 8.48

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Phosalacine;
IUPAC/Chemical Name
((2S)-2-amino-4-(hydroxy(methyl)phosphoryl)butanoyl)-L-alanyl-L-leucine
InChi Key
GRIZBDACBCXJCF-DCAQKATOSA-N
InChi Code
InChI=1S/C14H28N3O6P/c1-8(2)7-11(14(20)21)17-12(18)9(3)16-13(19)10(15)5-6-24(4,22)23/h8-11H,5-7,15H2,1-4H3,(H,16,19)(H,17,18)(H,20,21)(H,22,23)/t9-,10-,11-/m0/s1
SMILES Code
[C@H](NC([C@@H](NC([C@H](CCP(C)(=O)O)N)=O)C)=O)(CC(C)C)C(O)=O
Appearance
Solid powder
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 365.36 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.

Recalculate based on batch purity %
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: Omura S, Murata M, Hanaki H, Hinotozawa K, Oiwa R, Tanaka H. Phosalacine, a new herbicidal antibiotic containing phosphinothricin. Fermentation, isolation, biological activity and mechanism of action. J Antibiot (Tokyo). 1984 Aug;37(8):829-35. PubMed PMID: 6480502. 2: Blodgett JA, Zhang JK, Yu X, Metcalf WW. Conserved biosynthetic pathways for phosalacine, bialaphos and newly discovered phosphonic acid natural products. J Antibiot (Tokyo). 2016 Jan;69(1):15-25. doi: 10.1038/ja.2015.77. Epub 2015 Sep 2. PubMed PMID: 26328935; PubMed Central PMCID: PMC4731264. 3: Omura S, Hinotozawa K, Imamura N, Murata M. The structure of phosalacine, a new herbicidal antibiotic containing phosphinothricin. J Antibiot (Tokyo). 1984 Aug;37(8):939-40. PubMed PMID: 6480509. 4: Werner WJ, Allen KD, Hu K, Helms GL, Chen BS, Wang SC. In vitro phosphinate methylation by PhpK from Kitasatospora phosalacinea. Biochemistry. 2011 Oct 25;50(42):8986-8. doi: 10.1021/bi201220r. Epub 2011 Sep 28. PubMed PMID: 21950770; PubMed Central PMCID: PMC3214642.