WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 565405
CAS#: 155547-95-8
Description: Zwittermicin A is a natural antibiotic with diverse biological activities including broad-spectrum antibiosis against Bacteria and lower Eukarya, plant disease suppression, and enhancement of the insecticidal activity of Bacillus thuringiensis toxin against lepidopteran larvae.
MedKoo Cat#: 565405
Name: Zwittermicin A
CAS#: 155547-95-8
Chemical Formula: C13H28N6O8
Exact Mass: 396.1969
Molecular Weight: 396.4
Elemental Analysis: C, 39.39; H, 7.12; N, 21.20; O, 32.29
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Synonym: Zwittermicin A
IUPAC/Chemical Name: (2R,3S,4S,5S,7S,8R)-4,8-Diamino-N-[(2S)-1-amino-3-(carbamoylamino)-1-oxopropan-2-yl]-2,3,5,7,9-pentahydroxynonanamide
InChi Key: FYIPKJHNWFVEIR-FXQWNPMTSA-N
InChi Code: InChI=1S/C13H28N6O8/c14-4(3-20)6(21)1-7(22)8(15)9(23)10(24)12(26)19-5(11(16)25)2-18-13(17)27/h4-10,20-24H,1-3,14-15H2,(H2,16,25)(H,19,26)(H3,17,18,27)/t4-,5+,6+,7+,8+,9+,10-/m1/s1
SMILES Code: O=C(N[C@@H](CNC(N)=O)C(N)=O)[C@H](O)[C@@H](O)[C@@H](N)[C@@H](O)C[C@H](O)[C@H](N)CO
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: 2934.99.9001
The following data is based on the product molecular weight 396.4 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: Hao Z, Yan L, Liu J, Song F, Zhang J, Li X. Extraction of antibiotic zwittermicin A from Bacillus thuringiensis by macroporous resin and silica gel column chromatography. Biotechnol Appl Biochem. 2015 May-Jun;62(3):369-74. doi: 10.1002/bab.1277. Epub 2014 Sep 5. PubMed PMID: 25099664.
2: Luo Y, Ruan LF, Zhao CM, Wang CX, Peng DH, Sun M. Validation of the intact zwittermicin A biosynthetic gene cluster and discovery of a complementary resistance mechanism in Bacillus thuringiensis. Antimicrob Agents Chemother. 2011 Sep;55(9):4161-9. doi: 10.1128/AAC.00111-11. Epub 2011 Jul 5. PubMed PMID: 21730118; PubMed Central PMCID: PMC3165285.
3: Muchalski H, Hong KB, Johnston JN. Brønsted acid-promoted azide-olefin [3 + 2] cycloadditions for the preparation of contiguous aminopolyols: The importance of disiloxane ring size to a diastereoselective, bidirectional approach to zwittermicin A. Beilstein J Org Chem. 2010 Dec 20;6:1206-10. doi: 10.3762/bjoc.6.138. PubMed PMID: 21283562; PubMed Central PMCID: PMC3028999.
4: Chan YA, Thomas MG. Recognition of (2S)-aminomalonyl-acyl carrier protein (ACP) and (2R)-hydroxymalonyl-ACP by acyltransferases in zwittermicin A biosynthesis. Biochemistry. 2010 May 4;49(17):3667-77. doi: 10.1021/bi100141n. PubMed PMID: 20353188; PubMed Central PMCID: PMC2860681.
5: Rogers EW, Dalisay DS, Molinski TF. Zwittermicin A: synthesis of analogs and structure-activity studies. Bioorg Med Chem Lett. 2010 Apr 1;20(7):2183-5. doi: 10.1016/j.bmcl.2010.02.032. Epub 2010 Feb 11. PubMed PMID: 20189808; PubMed Central PMCID: PMC2845154.
6: Rogers EW, Molinski TF. (+)-Zwittermicin A. Rapid assembly of C9-C15 and a formal total synthesis. J Org Chem. 2009 Oct 16;74(20):7660-4. doi: 10.1021/jo901007v. PubMed PMID: 19746943; PubMed Central PMCID: PMC2759841.
7: Kevany BM, Rasko DA, Thomas MG. Characterization of the complete zwittermicin A biosynthesis gene cluster from Bacillus cereus. Appl Environ Microbiol. 2009 Feb;75(4):1144-55. doi: 10.1128/AEM.02518-08. Epub 2008 Dec 19. PubMed PMID: 19098220; PubMed Central PMCID: PMC2643575.
8: Chunxu S, Changming Z, Ziniu Y, Ming S. [Prediction, overexpression and activity confirmation of adenylation domain in Zwittermicin A biosynthesis gene cluster]. Wei Sheng Wu Xue Bao. 2008 Sep;48(9):1260-5. Chinese. PubMed PMID: 19062654.
9: Rogers EW, Dalisay DS, Molinski TF. (+)-Zwittermicin A: assignment of its complete configuration by total synthesis of the enantiomer and implication of D-serine in its biosynthesis. Angew Chem Int Ed Engl. 2008;47(42):8086-9. doi: 10.1002/anie.200801561. PubMed PMID: 18798190; PubMed Central PMCID: PMC3957322.
10: Zhao C, Song C, Luo Y, Yu Z, Sun M. L-2,3-diaminopropionate: one of the building blocks for the biosynthesis of Zwittermicin A in Bacillus thuringiensis subsp. kurstaki strain YBT-1520. FEBS Lett. 2008 Sep 3;582(20):3125-31. doi: 10.1016/j.febslet.2008.07.054. Epub 2008 Aug 8. PubMed PMID: 18692050.
11: Shao T, Bai L, Zhang J, Wang G, Liu D, Li Z, Liu J, Song F, Huang D. A nonribosomal peptide synthetase gene tzw1 is involved in zwittermicin A biosynthesis in Bacillus thuringiensis G03. Curr Microbiol. 2008 Jul;57(1):61-5. doi: 10.1007/s00284-008-9153-5. Epub 2008 Apr 30. PubMed PMID: 18446411.
12: Zhao C, Zeng H, Yu Z, Sun M. N-Acyl homoserine lactonase promotes prevention of Erwinia virulence with zwittermicin A-producing strain Bacillus cereus. Biotechnol Bioeng. 2008 Jun 15;100(3):599-603. doi: 10.1002/bit.21794. PubMed PMID: 18438870.
13: Rogers EW, Molinski TF. Asymmetric synthesis of diastereomeric diaminoheptanetetraols. A proposal for the configuration of (+)-zwittermicin a. Org Lett. 2007 Feb 1;9(3):437-40. PubMed PMID: 17249781; PubMed Central PMCID: PMC2729442.
14: Zhao C, Luo Y, Song C, Liu Z, Chen S, Yu Z, Sun M. Identification of three Zwittermicin A biosynthesis-related genes from Bacillus thuringiensis subsp. kurstaki strain YBT-1520. Arch Microbiol. 2007 Apr;187(4):313-9. Epub 2007 Jan 16. PubMed PMID: 17225146.
15: Nair JR, Narasimman G, Sekar V. Cloning and partial characterization of zwittermicin A resistance gene cluster from Bacillus thuringiensis subsp. kurstaki strain HD1. J Appl Microbiol. 2004;97(3):495-503. PubMed PMID: 15281929.
16: Emmert EA, Klimowicz AK, Thomas MG, Handelsman J. Genetics of zwittermicin a production by Bacillus cereus. Appl Environ Microbiol. 2004 Jan;70(1):104-13. PubMed PMID: 14711631; PubMed Central PMCID: PMC321298.
17: Stohl EA, Milner JL, Handelsman J. Zwittermicin A biosynthetic cluster. Gene. 1999 Sep 17;237(2):403-11. PubMed PMID: 10521664.
18: Stohl EA, Brady SF, Clardy J, Handelsman J. ZmaR, a novel and widespread antibiotic resistance determinant that acetylates zwittermicin A. J Bacteriol. 1999 Sep;181(17):5455-60. PubMed PMID: 10464220; PubMed Central PMCID: PMC94055.
19: Silo-Suh LA, Stabb EV, Raffel SJ, Handelsman J. Target range of zwittermicin A, an aminopolyol antibiotic from Bacillus cereus. Curr Microbiol. 1998 Jul;37(1):6-11. PubMed PMID: 9625782.
20: Stabb EV, Handelsman J. Genetic analysis of zwittermicin A resistance in Escherichia coli: effects on membrane potential and RNA polymerase. Mol Microbiol. 1998 Jan;27(2):311-22. PubMed PMID: 9484887.
