메뉴 건너뛰기




Volumn 14, Issue 24, 2006, Pages 8259-8270

An RNA polymerase inhibitor, cyclothiazomycin B1, and its isomer

Author keywords

Cyclic thiopeptide; Cyclothiazomycin B; Isomerization of dehydrohomoalanine; RNA polymerase inhibition

Indexed keywords

ANTIBIOTIC AGENT; CYCLOTHIAZOMYCIN B1; CYCLOTHIAZOMYCIN B2; ENZYME INHIBITOR; RNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 33750502619     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.09.006     Document Type: Article
Times cited : (37)

References (32)
  • 11
    • 0014669956 scopus 로고    scopus 로고
    • di Mauro, E.; Synder, L.; Marino, P.; Lamberti, A.; Coppo, A.; Tocchini-Valentini, G. P. N. Nature 1969, 222, 533-537.
  • 16
    • 33750507165 scopus 로고    scopus 로고
    • note
    • Aoki et al. also studied the hydrolysates of cyclothiazomycin (3) in their paper describing its structural elucidation. However, they isolated this unit in lactam form despite almost identical degradation conditions. The reason for these differences is unclear.
  • 17
    • 33750507405 scopus 로고    scopus 로고
    • note
    • Unfortunately, measurements at higher concentration did not provide useful data due to serious signal broadening as described.
  • 21
    • 33750528868 scopus 로고    scopus 로고
    • note
    • +, suggesting the occurrence of hydrolysis at the aminothioacetal moiety of the 'mAla'.
  • 24
    • 4644285613 scopus 로고    scopus 로고
    • It is under investigation by collaboration with Bagley et al. They have synthesized the corresponding lactam in optically active form:
    • It is under investigation by collaboration with Bagley et al. They have synthesized the corresponding lactam in optically active form:. Bagley M.C., Xiong X. Org. Lett. 6 (2004) 3401-3404
    • (2004) Org. Lett. , vol.6 , pp. 3401-3404
    • Bagley, M.C.1    Xiong, X.2
  • 25
    • 33750530509 scopus 로고    scopus 로고
    • note
    • Prior to the chemical shift predictions, structural optimization was performed employing ab initio 6-31G* for each model compound. We used Spartan '04 program by Wavefunction Inc. (18401 Von Karman Avenue, Suite 370 Irvine, CA 92612).
  • 26
    • 33750494660 scopus 로고    scopus 로고
    • note
    • The theoretical chemical shifts predictions suggested the olefinic protons of (E)-DHHA residues appear ca. 1.0 ppm lower field than that of the corresponding (Z)-DHHA residues for other model compounds as shown below. These calculations also indicated that (Z)-DHHA residues are ca. 2.5 kcal/mol sterically more stable than the (E)-DHHA residues. These results also are consisent with our assumption for the stereochemistry of DHHA2 moiety in 1 and 2.
  • 30
    • 0031591384 scopus 로고    scopus 로고
    • Zhang, X.; Studier, F. W. J. Mol. Biol. 1997, 269, 10-27.
  • 32
    • 0025365183 scopus 로고    scopus 로고
    • note
    • +. These indicated the same mass number 1472, whereas the mass formula by Cooper was one carbon smaller than that of Aoki's 3. Cooper also disclosed existences of a dehydroalanine, two dehydrohomoalamnines, three thiazolines, and three thiazoles, which are the same residues as those involved in Aoki's 3. Physical properties of our 1 and 2 were rather similar to those in Copper's report: Cooper, R.; Truumees, I.; Barrett, T.; Patel, M.; Schwartz, J.; Puar, M.; Das, P.; Pramanik, B. J. Antibiot. 1990, 43, 897.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.