MedKoo Cat#: 563084 | Name: Nocardicin A

Description:

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

Nocardicin A is a moderate antibiotic agent against a broad spectrum of gram-negative bacteria.

Chemical Structure

Nocardicin A
Nocardicin A
CAS#39391-39-4

Theoretical Analysis

MedKoo Cat#: 563084

Name: Nocardicin A

CAS#: 39391-39-4

Chemical Formula: C23H24N4O9

Exact Mass: 500.1543

Molecular Weight: 500.46

Elemental Analysis: C, 55.20; H, 4.83; N, 11.20; O, 28.77

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
Nocardicin A; Nocardicin-A;
IUPAC/Chemical Name
(2R)-2-Amino-4-[4-[(Z)-C-[[(3S)-1-[(R)-carboxy-(4-hydroxyphenyl)methyl]-2-oxoazetidin-3-yl]carbamoyl]-N-hydroxycarbonimidoyl]phenoxy]butanoic acid
InChi Key
CTNZOGJNVIFEBA-UPSUJEDGSA-N
InChi Code
InChI=1S/C23H24N4O9/c24-16(22(31)32)9-10-36-15-7-3-12(4-8-15)18(26-35)20(29)25-17-11-27(21(17)30)19(23(33)34)13-1-5-14(28)6-2-13/h1-8,16-17,19,28,35H,9-11,24H2,(H,25,29)(H,31,32)(H,33,34)/b26-18-/t16-,17+,19-/m1/s1
SMILES Code
O=C(O)[C@H](N)CCOC1=CC=C(/C(C(N[C@@H]2C(N([C@@H](C(O)=O)C3=CC=C(O)C=C3)C2)=O)=O)=N/O)C=C1
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 500.46 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: Decuyper L, Deketelaere S, Vanparys L, Jukic M, Sosic I, Sauvage E, Amoroso AM, Verlaine O, Joris B, Gobec S, D'hooghe M. In silico design and enantioselective synthesis of functionalized monocyclic 3-amino-1-carboxymethyl-β-lactams as inhibitors of penicillin-binding proteins of resistant bacteria. Chemistry. 2018 Jun 8. doi: 10.1002/chem.201801868. [Epub ahead of print] PubMed PMID: 29882610. 2: Gaudelli NM, Long DH, Townsend CA. β-Lactam formation by a non-ribosomal peptide synthetase during antibiotic biosynthesis. Nature. 2015 Apr 16;520(7547):383-7. doi: 10.1038/nature14100. Epub 2015 Jan 26. PubMed PMID: 25624104; PubMed Central PMCID: PMC4401618. 3: Gaudelli NM, Townsend CA. Epimerization and substrate gating by a TE domain in β-lactam antibiotic biosynthesis. Nat Chem Biol. 2014 Apr;10(4):251-8. doi: 10.1038/nchembio.1456. Epub 2014 Feb 16. PubMed PMID: 24531841; PubMed Central PMCID: PMC3961552. 4: Gaudelli NM, Townsend CA. Stereocontrolled syntheses of peptide thioesters containing modified seryl residues as probes of antibiotic biosynthesis. J Org Chem. 2013 Jul 5;78(13):6412-26. doi: 10.1021/jo4007893. Epub 2013 Jun 18. Erratum in: J Org Chem. 2013 Nov 1;78(21):11115. PubMed PMID: 23758494; PubMed Central PMCID: PMC3898789. 5: Davidsen JM, Bartley DM, Townsend CA. Non-ribosomal propeptide precursor in nocardicin A biosynthesis predicted from adenylation domain specificity dependent on the MbtH family protein NocI. J Am Chem Soc. 2013 Feb 6;135(5):1749-59. doi: 10.1021/ja307710d. Epub 2013 Jan 18. PubMed PMID: 23330869; PubMed Central PMCID: PMC3571714. 6: Giessen TW, Franke KB, Knappe TA, Kraas FI, Bosello M, Xie X, Linne U, Marahiel MA. Isolation, structure elucidation, and biosynthesis of an unusual hydroxamic acid ester-containing siderophore from Actinosynnema mirum. J Nat Prod. 2012 May 25;75(5):905-14. doi: 10.1021/np300046k. Epub 2012 May 11. PubMed PMID: 22578145. 7: Davidsen JM, Townsend CA. In vivo characterization of nonribosomal peptide synthetases NocA and NocB in the biosynthesis of nocardicin A. Chem Biol. 2012 Feb 24;19(2):297-306. doi: 10.1016/j.chembiol.2011.10.020. PubMed PMID: 22365611; PubMed Central PMCID: PMC3292777. 8: Land M, Lapidus A, Mayilraj S, Chen F, Copeland A, Del Rio TG, Nolan M, Lucas S, Tice H, Cheng JF, Chertkov O, Bruce D, Goodwin L, Pitluck S, Rohde M, Göker M, Pati A, Ivanova N, Mavromatis K, Chen A, Palaniappan K, Hauser L, Chang YJ, Jeffries CC, Brettin T, Detter JC, Han C, Chain P, Tindall BJ, Bristow J, Eisen JA, Markowitz V, Hugenholtz P, Kyrpides NC, Klenk HP. Complete genome sequence of Actinosynnema mirum type strain (101). Stand Genomic Sci. 2009 Jul 20;1(1):46-53. doi: 10.4056/sigs.21137. PubMed PMID: 21304636; PubMed Central PMCID: PMC3035213. 9: Davidsen JM, Townsend CA. Identification and characterization of NocR as a positive transcriptional regulator of the beta-lactam nocardicin A in Nocardia uniformis. J Bacteriol. 2009 Feb;191(3):1066-77. doi: 10.1128/JB.01833-07. Epub 2008 Nov 21. PubMed PMID: 19028891; PubMed Central PMCID: PMC2632093. 10: Kelly WL, Townsend CA. Mutational analysis of nocK and nocL in the nocardicin a producer Nocardia uniformis. J Bacteriol. 2005 Jan;187(2):739-46. PubMed PMID: 15629944; PubMed Central PMCID: PMC543527. 11: Gunsior M, Breazeale SD, Lind AJ, Ravel J, Janc JW, Townsend CA. The biosynthetic gene cluster for a monocyclic beta-lactam antibiotic, nocardicin A. Chem Biol. 2004 Jul;11(7):927-38. PubMed PMID: 15271351. 12: Kelly WL, Townsend CA. Mutational analysis and characterization of nocardicin C-9' epimerase. J Biol Chem. 2004 Sep 10;279(37):38220-7. Epub 2004 Jul 13. PubMed PMID: 15252031. 13: Hwu JR, Ethiraj KS, Hakimelahi GH. Biological activity of some monocyclic- and bicyclic beta-lactams with specified functional groups. Mini Rev Med Chem. 2003 Jun;3(4):305-13. Review. PubMed PMID: 12678824. 14: Kelly WL, Townsend CA. Role of the cytochrome P450 NocL in nocardicin A biosynthesis. J Am Chem Soc. 2002 Jul 17;124(28):8186-7. PubMed PMID: 12105888. 15: Gerardin-Charbonnier C, Auberger S, Molina L, Achilefu S, Manresa MA, Vinardell P, Infante MR, Selve C. Preparation and antibiotic activity of monobactam analogues of nocardicins. Prep Biochem Biotechnol. 1999 Aug;29(3):257-72. PubMed PMID: 10431930. 16: Reeve AM, Breazeale SD, Townsend CA. Purification, characterization, and cloning of an S-adenosylmethionine-dependent 3-amino-3-carboxypropyltransferase in nocardicin biosynthesis. J Biol Chem. 1998 Nov 13;273(46):30695-703. PubMed PMID: 9804844. 17: Méndez R, Alemany T, Martín-Villacorta J. Catalysis of hydrolysis and aminolysis of non-classical beta-lactam antibiotics by metal ions and metal chelates. Chem Pharm Bull (Tokyo). 1992 Dec;40(12):3228-33. PubMed PMID: 1294325. 18: Méndez R, Alemany T, Martín-Villacorta J. Stability in aqueous solution of two monocyclic beta-lactam antibiotics: aztreonam and nocardicin A. Chem Pharm Bull (Tokyo). 1992 Dec;40(12):3222-7. PubMed PMID: 1294324. 19: Ursinus A, Steinhaus H, Höltje JV. Purification of a nocardicin A-sensitive LD-carboxypeptidase from Escherichia coli by affinity chromatography. J Bacteriol. 1992 Jan;174(2):441-6. PubMed PMID: 1729236; PubMed Central PMCID: PMC205735. 20: Chitnis SN, Prasad KS, Bhargava PM. Isolation and characterization of autolysis-defective mutants of Escherichia coli that are resistant to the lytic activity of seminalplasmin. J Gen Microbiol. 1990 Mar;136(3):463-9. PubMed PMID: 1697323.