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MedKoo Cat#: 596865 | Name: Agrocinopine

Description:

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

Agrocinopine is an Opine phosphorylated sugar synthesized by crown gall tumors & utilized as nutrient source by bacteria responsible for infection.

Chemical Structure

Agrocinopine
Agrocinopine
CAS#77193-02-3

Theoretical Analysis

MedKoo Cat#: 596865

Name: Agrocinopine

CAS#: 77193-02-3

Chemical Formula: C17H31O18P

Exact Mass: 554.1248

Molecular Weight: 554.39

Elemental Analysis: C, 36.83; H, 5.64; O, 51.95; P, 5.59

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 #
No Data
Synonym
Agrocinopine; Agrocinopine A;
IUPAC/Chemical Name
(2R,3S,4S,5S)-4-hydroxy-2,5-bis(hydroxymethyl)-5-(((2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)tetrahydrofuran-3-yl ((2R,3S,4S)-3,4,5-trihydroxy-1-oxopentan-2-yl) hydrogen (R)-phosphate
InChi Key
MQDWDXNPTQNPOZ-HKJCQTGWSA-N
InChi Code
InChI=1S/C17H31O18P/c18-1-6(23)10(24)8(3-20)34-36(29,30)35-14-9(4-21)32-17(5-22,15(14)28)33-16-13(27)12(26)11(25)7(2-19)31-16/h3,6-16,18-19,21-28H,1-2,4-5H2,(H,29,30)/t6-,7-,8-,9+,10-,11+,12-,13+,14+,15-,16+,17-/m0/s1
SMILES Code
O=[P@](O[C@H]1[C@H](O)[C@](CO)(O[C@@H]2[C@H](O)[C@@H](O)[C@@H]([C@@H](O2)CO)O)O[C@@H]1CO)(O)O[C@@H](C=O)[C@H]([C@H](CO)O)O
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 554.39 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
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Concerted transfer of the virulence Ti plasmid and companion At plasmid in the Agrobacterium tumefaciens-induced plant tumour. Mol Microbiol. 2013 Dec;90(6):1178-89. doi: 10.1111/mmi.12423. Epub 2013 Oct 31. PubMed PMID: 24118167. 4: Haudecoeur E, Faure D. A fine control of quorum-sensing communication in Agrobacterium tumefaciens. Commun Integr Biol. 2010 Mar;3(2):84-8. PubMed PMID: 20585496; PubMed Central PMCID: PMC2889960. 5: Haudecoeur E, Tannières M, Cirou A, Raffoux A, Dessaux Y, Faure D. Different regulation and roles of lactonases AiiB and AttM in Agrobacterium tumefaciens C58. Mol Plant Microbe Interact. 2009 May;22(5):529-37. doi: 10.1094/MPMI-22-5-0529. PubMed PMID: 19348571. 6: Kim HS, Yi H, Myung J, Piper KR, Farrand SK. Opine-based Agrobacterium competitiveness: dual expression control of the agrocinopine catabolism (acc) operon by agrocinopines and phosphate levels. J Bacteriol. 2008 May;190(10):3700-11. doi: 10.1128/JB.00067-08. Epub 2008 Mar 14. PubMed PMID: 18344359; PubMed Central PMCID: PMC2395003. 7: Oger P, Farrand SK. Two opines control conjugal transfer of an Agrobacterium plasmid by regulating expression of separate copies of the quorum-sensing activator gene traR. J Bacteriol. 2002 Feb;184(4):1121-31. PubMed PMID: 11807073; PubMed Central PMCID: PMC134798. 8: Oger P, Farrand SK. Co-evolution of the agrocinopine opines and the agrocinopine-mediated control of TraR, the quorum-sensing activator of the Ti plasmid conjugation system. Mol Microbiol. 2001 Sep;41(5):1173-85. PubMed PMID: 11555296. 9: Otten L, Salomone JY, Helfer A, Schmidt J, Hammann P, De Ruffray P. Sequence and functional analysis of the left-hand part of the T-region from the nopaline-type Ti plasmid, pTiC58. Plant Mol Biol. 1999 Dec;41(6):765-76. PubMed PMID: 10737141. 10: Piper KR, Farrand SK. Quorum sensing but not autoinduction of Ti plasmid conjugal transfer requires control by the opine regulon and the antiactivator TraM. J Bacteriol. 2000 Feb;182(4):1080-8. PubMed PMID: 10648535; PubMed Central PMCID: PMC94385. 11: Piper KR, Beck Von Bodman S, Hwang I, Farrand SK. Hierarchical gene regulatory systems arising from fortuitous gene associations: controlling quorum sensing by the opine regulon in Agrobacterium. Mol Microbiol. 1999 Jun;32(5):1077-89. PubMed PMID: 10361309. 12: Kim H, Farrand SK. Opine catabolic loci from Agrobacterium plasmids confer chemotaxis to their cognate substrates. Mol Plant Microbe Interact. 1998 Feb;11(2):131-43. PubMed PMID: 9450336. 13: Kim H, Farrand SK. Characterization of the acc operon from the nopaline-type Ti plasmid pTiC58, which encodes utilization of agrocinopines A and B and susceptibility to agrocin 84. J Bacteriol. 1997 Dec;179(23):7559-72. PubMed PMID: 9393724; PubMed Central PMCID: PMC179710. 14: Zeng G, Ye S, Larson TJ. Repressor for the sn-glycerol 3-phosphate regulon of Escherichia coli K-12: primary structure and identification of the DNA-binding domain. J Bacteriol. 1996 Dec;178(24):7080-9. PubMed PMID: 8955387; PubMed Central PMCID: PMC178618. 15: Swords KM, Dahlbeck D, Kearney B, Roy M, Staskawicz BJ. Spontaneous and induced mutations in a single open reading frame alter both virulence and avirulence in Xanthomonas campestris pv. vesicatoria avrBs2. J Bacteriol. 1996 Aug;178(15):4661-9. PubMed PMID: 8755898; PubMed Central PMCID: PMC178237. 16: Broer I, Dröge-Laser W, Barker RF, Neumann K, Klipp W, Pühler A. Identification of the Agrobacterium tumefaciens C58 T-DNA genes e and f and their impact on crown gall tumour formation. Plant Mol Biol. 1995 Jan;27(1):41-57. PubMed PMID: 7865795. 17: Hayman GT, Beck von Bodman S, Kim H, Jiang P, Farrand SK. Genetic analysis of the agrocinopine catabolic region of Agrobacterium tumefaciens Ti plasmid pTiC58, which encodes genes required for opine and agrocin 84 transport. J Bacteriol. 1993 Sep;175(17):5575-84. PubMed PMID: 8366042; PubMed Central PMCID: PMC206614. 18: Paulus F, Otten L. Functional and mutated agrocinopine synthase genes on octopine T-DNAs. Mol Plant Microbe Interact. 1993 May-Jun;6(3):393-402. PubMed PMID: 8324252. 19: Beck von Bodman S, Hayman GT, Farrand SK. Opine catabolism and conjugal transfer of the nopaline Ti plasmid pTiC58 are coordinately regulated by a single repressor. Proc Natl Acad Sci U S A. 1992 Jan 15;89(2):643-7. PubMed PMID: 1731335; PubMed Central PMCID: PMC48295. 20: Hayman GT, Farrand SK. Agrobacterium plasmids encode structurally and functionally different loci for catabolism of agrocinopine-type opines. Mol Gen Genet. 1990 Sep;223(3):465-73. PubMed PMID: 2270086.