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MedKoo Cat#: 561775 | Name: Sulfazecin free acid

Description:

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

Sulfazecin is a β-Lactam antibiotic against multi-drug resistant pathogens.

Chemical Structure

Sulfazecin free acid
Sulfazecin free acid
CAS#77912-79-9 (free acid)

Theoretical Analysis

MedKoo Cat#: 561775

Name: Sulfazecin free acid

CAS#: 77912-79-9 (free acid)

Chemical Formula: C12H20N4O9S

Exact Mass: 396.0951

Molecular Weight: 396.37

Elemental Analysis: C, 36.36; H, 5.09; N, 14.14; O, 36.33; S, 8.09

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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Related CAS #
79194-40-4 (methanolate) 79720-09-5 (potassium) 80734-22-1 (sodium) 77912-79-9 (free acid)
Synonym
Antibiotic EM 5210; Antibiotic G 6302; G6302; G-6302; Sulfazecin;
IUPAC/Chemical Name
N5-((R)-1-(((R)-3-methoxy-2-oxo-1-sulfoazetidin-3-yl)amino)-1-oxopropan-2-yl)-D-glutamine
InChi Key
MOBOUQJWGBVNCR-NQYJQULFSA-N
InChi Code
InChI=1S/C12H20N4O9S/c1-6(14-8(17)4-3-7(13)10(19)20)9(18)15-12(25-2)5-16(11(12)21)26(22,23)24/h6-7H,3-5,13H2,1-2H3,(H,14,17)(H,15,18)(H,19,20)(H,22,23,24)/t6-,7-,12-/m1/s1
SMILES Code
C[C@H](C(=O)N[C@]1(CN(C1=O)S(=O)(=O)O)OC)NC(=O)CC[C@H](C(=O)O)N
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
>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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 396.37 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: Oliver RA, Li R, Townsend CA. Monobactam formation in sulfazecin by a nonribosomal peptide synthetase thioesterase. Nat Chem Biol. 2018 Jan;14(1):5-7. doi: 10.1038/nchembio.2526. Epub 2017 Nov 20. PubMed PMID: 29155429; PubMed Central PMCID: PMC5726899. 2: Horsman ME, Marous DR, Li R, Oliver RA, Byun B, Emrich SJ, Boggess B, Townsend CA, Mobashery S. Whole-Genome Shotgun Sequencing of Two β-Proteobacterial Species in Search of the Bulgecin Biosynthetic Cluster. ACS Chem Biol. 2017 Oct 20;12(10):2552-2557. doi: 10.1021/acschembio.7b00687. Epub 2017 Sep 26. PubMed PMID: 28937735; PubMed Central PMCID: PMC5653948. 3: Braga D, Lackner G. One Ring to Fight Them All: The Sulfazecin Story. Cell Chem Biol. 2017 Jan 19;24(1):1-2. doi: 10.1016/j.chembiol.2017.01.001. PubMed PMID: 28107651. 4: Li R, Oliver RA, Townsend CA. Identification and Characterization of the Sulfazecin Monobactam Biosynthetic Gene Cluster. Cell Chem Biol. 2017 Jan 19;24(1):24-34. doi: 10.1016/j.chembiol.2016.11.010. Epub 2016 Dec 22. PubMed PMID: 28017601; PubMed Central PMCID: PMC5286544. 5: Box SJ, Brown AG, Gilpin ML, Gwynn MN, Spear SR. MM 42842, a new member of the monobactam family produced by Pseudomonas cocovenenans. II. Production, isolation and properties of MM 42842. J Antibiot (Tokyo). 1988 Jan;41(1):7-12. PubMed PMID: 3346195. 6: Parker WL, O'Sullivan J, Sykes RB. Naturally occurring monobactams. Adv Appl Microbiol. 1986;31:181-205. Review. PubMed PMID: 3521210. 7: Okonogi K, Sugiura A, Kuno M, Ono H, Harada S, Higashide E. Interactions of formylamino- and methoxy-substituted beta-lactam antibiotics with beta-lactamases. J Antibiot (Tokyo). 1985 Nov;38(11):1555-63. PubMed PMID: 3878359. 8: Imada A, Kondo M, Okonogi K, Yukishige K, Kuno M. In vitro and in vivo antibacterial activities of carumonam (AMA-1080), a new N-sulfonated monocyclic beta-lactam antibiotic. Antimicrob Agents Chemother. 1985 May;27(5):821-7. PubMed PMID: 3874598; PubMed Central PMCID: PMC180159. 9: Sendai M, Hashiguchi S, Tomimoto M, Kishimoto S, Matsuo T, Kondo M, Ochiai M. Chemical modification of sulfazecin. Synthesis of 4-(substituted methyl)-2-azetidinone-1-sulfonic acid derivatives. J Antibiot (Tokyo). 1985 Mar;38(3):346-71. PubMed PMID: 4008329. 10: Kishimoto S, Sendai M, Tomimoto M, Hashiguchi S, Matsuo T, Ochiai M. Chemical modification of sulfazecin. Synthesis of 4-methoxycarbonyl-2-azetidinone-1-sulfonic acid derivatives. Chem Pharm Bull (Tokyo). 1984 Jul;32(7):2646-59. PubMed PMID: 6499083. 11: Kishimoto S, Sendai M, Hashiguchi S, Tomimoto M, Satoh Y, Matsuo T, Kondo M, Ochiai M. Synthesis of sulfazecin-type 2-azetidinones with a carbon substituent at the 4-position. J Antibiot (Tokyo). 1983 Oct;36(10):1421-4. PubMed PMID: 6358173. 12: Imada A, Kintaka K, Nakao M, Shinagawa S. Bulgecin, a bacterial metabolite which in concert with beta-lactam antibiotics causes bulge formation. J Antibiot (Tokyo). 1982 Oct;35(10):1400-3. PubMed PMID: 6757229. 13: Kintaka K, Haibara K, Asai M, Imada A. Isosulfazecin, a new beta-lactam antibiotic, produced by an acidophilic pseudomonad. Fermentation, isolation and characterization. J Antibiot (Tokyo). 1981 Sep;34(9):1081-9. PubMed PMID: 7328050. 14: Asai M, Haibara K, Muroi M, Kintaka K, Kishi T. Sulfazecin, a novel beta-lactam antibiotic of bacterial origin. Isolation and chemical characterization. J Antibiot (Tokyo). 1981 Jun;34(6):621-7. PubMed PMID: 7024230. 15: Imada A, Kitano K, Kintaka K, Muroi M, Asai M. Sulfazecin and isosulfazecin, novel beta-lactam antibiotics of bacterial origin. Nature. 1981 Feb 12;289(5798):590-1. PubMed PMID: 7007891.

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