Novel Bromotyrosine Alkaloids: Inhibitors of Mycothiol S-Conjugate Amidase

Organic Letters

Volumn 3, Issue 10, 2001, Pages 1543-1545

  Nicholas, Gillian M ^a   Newton, Gerald L ^b   Fahey, Robert C ^b   Bewley, Carole A ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMIDASE; ANTIINFECTIVE AGENT; DRUG DERIVATIVE; ENZYME INHIBITOR; MYCOTHIOL S CONJUGATE AMIDASE; MYCOTHIOL S-CONJUGATE AMIDASE; TYROSINE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPONGE (PORIFERA);

ALKALOIDS; AMIDOHYDROLASES; ANIMALS; ANTI-INFECTIVE AGENTS; ENZYME INHIBITORS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PORIFERA; TYROSINE;

EID: 0035902239     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015845+     Document Type: Article

References (22)

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9. Extract obtained from the NCI open repository.
10. 2155 and purified as described in ref 2.
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13. Compounds 1, 2, 4, and 5 inhibited mycothiol 5-conjugate amidase by 50% at 2, 100, 3, and 37 mM. respectively. A full report of biological data will be reported elsewere.
14. + m/z 680.9940, calcd 680.9944.
15. 1H NMR or HSQC spectra.
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17. 20D - 150° (c 0.19, MeOH); CD (MeOH) λ 260 nm Δ∈ -2.1, 292 nm ∈Δ -2.8 (see Supporting Information for spectrum).
18. max 238 nm (∈ 32000), 280 nm (∈ 20000), 340 nm (∈ 2800); CD (MeOH) λ 290 nm Δ∈ -2.7, 260 nm Δ∈ -1.0 (see Supporting Information for spectrum).
19. Litaudon, M.; Guyot, M. Tetrahedron Lett. 1986, 27, 4455.
20. + m/z 521, 523, 525 in a ratio of 1:2:1.
21. -1.
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