IUPAC/Chemical Name
Muramic acid, delta-lactam
InChi Key
KLOQXEJISMWHGN-SNTDCUFQSA-N
InChi Code
InChI=1S/C9H16N2O6/c1-3-7(14)11-9(17-3)5(10)8(15)16-4(2-12)6(9)13/h3-6,8,12-13,15H,2,10H2,1H3,(H,11,14)/t3?,4-,5+,6-,8+,9-/m1/s1
SMILES Code
CC(O[C@@]12[C@@H]([C@H](O[C@@H]([C@@H]1N)O)CO)O)C(N2)=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
2934.99.9001
Preparing Stock Solutions
The following data is based on the
product
molecular weight
248.24
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: Coullon H, Rifflet A, Wheeler R, Janoir C, Boneca IG, Candela T. N-Deacetylases required for muramic-δ-lactam production are involved in Clostridium difficile sporulation, germination, and heat resistance. J Biol Chem. 2018 Nov 23;293(47):18040-18054. doi: 10.1074/jbc.RA118.004273. Epub 2018 Sep 28. PMID: 30266804; PMCID: PMC6254358.
2: Gilmore ME, Bandyopadhyay D, Dean AM, Linnstaedt SD, Popham DL. Production of muramic delta-lactam in Bacillus subtilis spore peptidoglycan. J Bacteriol. 2004 Jan;186(1):80-9. doi: 10.1128/jb.186.1.80-89.2004. PMID: 14679227; PMCID: PMC303458.
3: Popham DL, Helin J, Costello CE, Setlow P. Muramic lactam in peptidoglycan of Bacillus subtilis spores is required for spore outgrowth but not for spore dehydration or heat resistance. Proc Natl Acad Sci U S A. 1996 Dec 24;93(26):15405-10. doi: 10.1073/pnas.93.26.15405. PMID: 8986824; PMCID: PMC26417.
4: Wickus GG, Warth AD, Strominger JL. Appearance of muramic lactam during cortex synthesis in sporulating cultures of Bacillus cereus and Bacillus megaterium. J Bacteriol. 1972 Aug;111(2):625-7. PMID: 4626506; PMCID: PMC251327.
5: Fukushima T, Yamamoto H, Atrih A, Foster SJ, Sekiguchi J. A polysaccharide deacetylase gene (pdaA) is required for germination and for production of muramic delta-lactam residues in the spore cortex of Bacillus subtilis. J Bacteriol. 2002 Nov;184(21):6007-15. doi: 10.1128/jb.184.21.6007-6015.2002. PMID: 12374835; PMCID: PMC135383.
6: Popham DL, Helin J, Costello CE, Setlow P. Analysis of the peptidoglycan structure of Bacillus subtilis endospores. J Bacteriol. 1996 Nov;178(22):6451-8. doi: 10.1128/jb.178.22.6451-6458.1996. PMID: 8932300; PMCID: PMC178530.
7: Faille C, Ronse A, Dewailly E, Slomianny C, Maes E, Krzewinski F, Guerardel Y. Presence and function of a thick mucous layer rich in polysaccharides around Bacillus subtilis spores. Biofouling. 2014;30(7):845-58. doi: 10.1080/08927014.2014.939073. PMID: 25115519.
8: Lambert EA, Sherry N, Popham DL. In vitro and in vivo analyses of the Bacillus anthracis spore cortex lytic protein SleL. Microbiology. 2012 May;158(Pt 5):1359-1368. doi: 10.1099/mic.0.056630-0. Epub 2012 Feb 16. PMID: 22343356; PMCID: PMC3542826.
9: Dowd MM, Orsburn B, Popham DL. Cortex peptidoglycan lytic activity in germinating Bacillus anthracis spores. J Bacteriol. 2008 Jul;190(13):4541-8. doi: 10.1128/JB.00249-08. Epub 2008 May 2. PMID: 18456807; PMCID: PMC2446819.
10: Imae Y, Strominger JL. Cortex content of asporogenous mutants of Bacillus subtilis. J Bacteriol. 1976 May;126(2):914-8. PMID: 1262319; PMCID: PMC233229.
11: Imae Y, Strominger JL. Conditional spore cortex-less mutants of Bacillus sphaericus 9602. J Biol Chem. 1976 Mar 10;251(5):1493-9. PMID: 767335.
12: Imae Y, Strominger JL. Relationship between cortex content and properties of Bacillus sphaericus spores. J Bacteriol. 1976 May;126(2):907-13. PMID: 944183; PMCID: PMC233228.
13: Mallidis CG, Scholefield J. Relation of the heat resistance of bacterial spores to chemical composition and structure. II. Relation to cortex and structure. J Appl Bacteriol. 1987 Sep;63(3):207-15. doi: 10.1111/j.1365-2672.1987.tb04938.x. PMID: 3429356.
