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Volumn , Issue 14, 2008, Pages 2122-2126

Synthesis of a biotin-labeled quorum-sensing molecule: Towards a general method for target identification

(9) Spandl, Richard J a Nicholson, Rebecca L a Marsden, David M a Hodgkinson, James T a Su, Xianbin a Thomas, Gemma L a Salmond, George P C a Welch, Martin a Spring, David R a

a UNIVERSITY OF CAMBRIDGE (United Kingdom)

Author keywords

Drugs; High throughput screening; OHHL; Proteins; Quorum sensing

Indexed keywords

BIOTIN; LACTONE DERIVATIVE; N (3 OXOHEXANOYL) LEVO HOMOSERINE LACTONE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; GEL ELECTROPHORESIS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; QUORUM SENSING;

EID: 51449095293 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1077978 Document Type: Article

Times cited : (9)

References (28)

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24
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- Analogues of the related signaling molecule N-3- (oxododecanoyl)-L-homoserine lactone (OdDHL), used in Pseudomonas aeruginosa, have been synthesized by coupling using the acid, Meldrum's acid, and the amine in one pot: Chhabra, S. R.; Harty, C.; Hooi, D. S. W.; Daykin, M.; Williams, P.; Telford, G.; Pritchard, D. I.; Bycroft, B. W. J. Med. Chem. 2003, 46, 97; in our hands this method proved less fruitful than the stepwise method employed therein.
- Analogues of the related signaling molecule N-3- (oxododecanoyl)-L-homoserine lactone (OdDHL), used in Pseudomonas aeruginosa, have been synthesized by coupling using the acid, Meldrum's acid, and the amine in one pot: Chhabra, S. R.; Harty, C.; Hooi, D. S. W.; Daykin, M.; Williams, P.; Telford, G.; Pritchard, D. I.; Bycroft, B. W. J. Med. Chem. 2003, 46, 97; in our hands this method proved less fruitful than the stepwise method employed therein.

25
- 51449120400
- N-(3-Oxohexanoyl)-L-homoserine lactone(2, R f, 0.23 (SiO2; EtOAc-PE, 8:2, IR (neat, νmax, 3301 (w, br, 2965 (w, 2878 (w, 1774 (s, 1716 (m, 1649 (s, 1535 (m, 1379 (m, 1221 (m, 1169 (s, 1021 (m) cm-1. 1H NMR (400 MHz, CDCl3, δ, 7.73 (1 H, br s, CONH, 4.63-4.51 [1 H, br m, C(2)H, 4.43 [1 H, br t, J, 9.1 Hz, C(4)H aHb, 4.27-4.18 [1 H, br m, C(4)HaH b, 3.42 (2 H, s, COCH2CO, 2.68-2.58 [1 H, br m, C(3)HaHb, 2.47 (2 H, t, J, 7.3 Hz, CH 3CH2CH2, 2.30-2.16 [1 H, br m, C(3)H aHb, 1.54(2 H, sext, J, 7.3 Hz, CH 3CH2CH2, 0.86 (2 H, t, J, 7.5, CH 3CH2CH2, 13C NMR (100 MHz, CDCl3, δ, 206.1 (C, 175.2 (C, 166.9 C, 65.9
- 3).

26
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- Blackwell, H. E.; Geske, G. D.; Wezeman, R. J. WO 2006/084056 A2, 2006.
- Blackwell, H. E.; Geske, G. D.; Wezeman, R. J. WO 2006/084056 A2, 2006.

27
- 51449096778
- 3). Although some racemization may have occurred during the synthesis reported here, this did not affect binding of CarR. In our hands coupling with HOBt was less successful.
- 3). Although some racemization may have occurred during the synthesis reported here, this did not affect binding of CarR. In our hands coupling with HOBt was less successful.

28
- 51449115180
- Polymer-bound DMAP was required in the final EDC-mediated coupling to aid purification. The reaction products and DMAP had very similar R f values. Synthesis of 18 A round-bottom flask, equipped with a magnetic stirrer, containing the ester 17 (529 mg, 1.02 mmol, LiOH·H2O (98 mg, 2.33 mmol) and 66% aq MeOH (25 mL) was stirred at r.t. for 16 h. The solvent was removed in vacuo to give the lithium salt of the corresponding acid (structure not shown) as a white solid (550 mg, The salt was used in subsequent reactions without further purification. A round-bottom flask, equipped with a magnetic stirrer, containing the lithium salt (0.55 g, 1.09 mmol, EDC (0.27 g, 1.42 mmol, polymer-bound DMAP (5 mmol/g, 1.1 g, 5.46 mmol, and DMF (40 mL) was stirred at r.t. for 15 min before being charged with L-homoserine lactone hydrobromide (1.02 g, 5.6 mmol) and stirred at r.t. for 16 h. The crude reaction mixture was filtered and solvent removed in vacuo
- 2).

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