Synonym
Alanylphosphatidylglycerol;
IUPAC/Chemical Name
(R)-3-(((S)-((R)-3-((L-alanyl)oxy)-2-hydroxypropoxy)(hydroxy)phosphoryl)oxy)propane-1,2-diyl didodecanoate
InChi Key
ZXAVHCQVHRXXOF-FRXPANAUSA-N
InChi Code
InChI=1S/C33H64NO11P/c1-4-6-8-10-12-14-16-18-20-22-31(36)41-26-30(45-32(37)23-21-19-17-15-13-11-9-7-5-2)27-44-46(39,40)43-25-29(35)24-42-33(38)28(3)34/h28-30,35H,4-27,34H2,1-3H3,(H,39,40)/t28-,29+,30+/m0/s1
SMILES Code
C[C@H](N)C(OC[C@@H](O)CO[P@@](OC[C@H](OC(CCCCCCCCCCC)=O)COC(CCCCCCCCCCC)=O)(O)=O)=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
>2 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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
681.84
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: Slavetinsky C, Kuhn S, Peschel A. Bacterial aminoacyl phospholipids - Biosynthesis and role in basic cellular processes and pathogenicity. Biochim Biophys Acta. 2017 Nov;1862(11):1310-1318. doi: 10.1016/j.bbalip.2016.11.013. Epub 2016 Dec 8. Review. PubMed PMID: 27940309.
2: Smith AM, Harrison JS, Grube CD, Sheppe AE, Sahara N, Ishii R, Nureki O, Roy H. tRNA-dependent alanylation of diacylglycerol and phosphatidylglycerol in Corynebacterium glutamicum. Mol Microbiol. 2015 Nov;98(4):681-93. doi: 10.1111/mmi.13150. Epub 2015 Sep 10. PubMed PMID: 26235234; PubMed Central PMCID: PMC4639916.
3: Slavetinsky CJ, Peschel A, Ernst CM. Alanyl-phosphatidylglycerol and lysyl-phosphatidylglycerol are translocated by the same MprF flippases and have similar capacities to protect against the antibiotic daptomycin in Staphylococcus aureus. Antimicrob Agents Chemother. 2012 Jul;56(7):3492-7. doi: 10.1128/AAC.00370-12. Epub 2012 Apr 9. PubMed PMID: 22491694; PubMed Central PMCID: PMC3393434.
4: Klein S, Lorenzo C, Hoffmann S, Walther JM, Storbeck S, Piekarski T, Tindall BJ, Wray V, Nimtz M, Moser J. Adaptation of Pseudomonas aeruginosa to various conditions includes tRNA-dependent formation of alanyl-phosphatidylglycerol. Mol Microbiol. 2009 Feb;71(3):551-65. doi: 10.1111/j.1365-2958.2008.06562.x. Epub 2008 Dec 14. PubMed PMID: 19087229.
5: Roy H, Dare K, Ibba M. Adaptation of the bacterial membrane to changing environments using aminoacylated phospholipids. Mol Microbiol. 2009 Feb;71(3):547-50. doi: 10.1111/j.1365-2958.2008.06563.x. Epub 2008 Dec 1. PubMed PMID: 19054327; PubMed Central PMCID: PMC2774118.
6: Fischer W, Arneth-Seifert D. D-Alanylcardiolipin, a major component of the unique lipid pattern of Vagococcus fluvialis. J Bacteriol. 1998 Jun;180(11):2950-7. PubMed PMID: 9603887; PubMed Central PMCID: PMC107264.
7: Sacré MM, El Mashak EM, Tocanne JF. A monolayer (pi,deltaV) study of the ionic properties of alanylphosphatidylglycerol: effects of pH and ions. Chem Phys Lipids. 1977 Dec;20(4):305-18. PubMed PMID: 23218.
8: dos Santos Mota JM, den Kamp JA, Verheij HM, van Deenen LL. Phospholipids of Streptococcus faecalis. J Bacteriol. 1970 Nov;104(2):611-9. PubMed PMID: 4321329; PubMed Central PMCID: PMC285035.
