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Volumn 14, Issue 15, 2008, Pages 4475-4478

Protection by conformationally restricted mobility: First solid-phase synthesis of triostin A

Author keywords

Conformation analysis; Peptides ?protecting groups; Solid phase synthesis; Triostin

Indexed keywords

AMINES; HIGH ENERGY PHYSICS; RISK ASSESSMENT;

EID: 54349091308     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200800372     Document Type: Article
Times cited : (14)

References (42)
  • 11
    • 34247891594 scopus 로고    scopus 로고
    • J. Tulla-Puche, N. Bayo-Puxan, Juan A. Moreno, Andres M. Francesc, C. Cuevas, M. Alvarez, F. Albericio, J. Am. Chem. Soc. 2007, 129, 5322-5323.
    • J. Tulla-Puche, N. Bayo-Puxan, Juan A. Moreno, Andres M. Francesc, C. Cuevas, M. Alvarez, F. Albericio, J. Am. Chem. Soc. 2007, 129, 5322-5323.
  • 25
    • 0017404351 scopus 로고    scopus 로고
    • In the course of studying its mode of action, analogues with less degree of N-methylation were synthesized. Thus, considerable attention has received the desmethylated triostin A TANDEM, T. L. Ciardelli, R. K. Olsen, J. Am. Chem. Soc. 1977, 99, 2806-2807
    • In the course of studying its mode of action, analogues with less degree of N-methylation were synthesized. Thus, considerable attention has received the desmethylated triostin A (TANDEM), [T. L. Ciardelli, R. K. Olsen, J. Am. Chem. Soc. 1977, 99, 2806-2807]
  • 26
    • 0018216196 scopus 로고    scopus 로고
    • and modifications on it such as the bis L-Ser TANDEM [T. L. Ciardelli, P. K. Chakravarty, R. K. Olsen, J. Am. Chem. Soc. 1978, 100, 7684-7690]
    • and modifications on it such as the bis L-Ser TANDEM [T. L. Ciardelli, P. K. Chakravarty, R. K. Olsen, J. Am. Chem. Soc. 1978, 100, 7684-7690]
  • 27
    • 2442646483 scopus 로고    scopus 로고
    • and the TANDEM with nucleobases [B. K. Lorenz,; U. Diederichsen, J. Org. Chem. 2004, 69, 3917-3927;
    • and the TANDEM with nucleobases [B. K. Lorenz,; U. Diederichsen, J. Org. Chem. 2004, 69, 3917-3927;
  • 29
    • 0034703449 scopus 로고    scopus 로고
    • Furthermore, an increase in conformational rigidity has been shown by the aza analogue of triostin A, azatriostin [D. L. Boger, J. K. Lee, J. Org. Chem. 2000, 65, 5996-6000]. All these synthesis had been carried in solution.
    • Furthermore, an increase in conformational rigidity has been shown by the aza analogue of triostin A, azatriostin [D. L. Boger, J. K. Lee, J. Org. Chem. 2000, 65, 5996-6000]. All these synthesis had been carried in solution.
  • 30
    • 24944438265 scopus 로고    scopus 로고
    • Syntheses on the solid-phase have been limited up to now to the desmethylated analogue of triostin (TANDEM) and to its aza derivative: a) J. P. Malkinson, M. K. Anim, M. Zloh, M. Searcey, J. Org. Chem. 2005, 70, 7654-7661;
    • Syntheses on the solid-phase have been limited up to now to the desmethylated analogue of triostin (TANDEM) and to its aza derivative: a) J. P. Malkinson, M. K. Anim, M. Zloh, M. Searcey, J. Org. Chem. 2005, 70, 7654-7661;
  • 34
    • 54349113274 scopus 로고    scopus 로고
    • Previous studies on N-methylated analogues had shown that the ester bond between the NMe-Val and the D-Ser was not stable to piperidine
    • Previous studies on N-methylated analogues had shown that the ester bond between the NMe-Val and the D-Ser was not stable to piperidine.
  • 35
    • 54349125520 scopus 로고    scopus 로고
    • Kociénsky [P. J. Kociénsky, Protecting groups, 3rd edition, Thieme, Stuttgart (Germany), 2004, pp. 29-32] describes several examples showing that a conformation change can produce new hindrance resulting in a modification of the regioselectivity or the stereospecificity, but to the best of our knowledge this is the first example of the new concept of protection.
    • Kociénsky [P. J. Kociénsky, Protecting groups, 3rd edition, Thieme, Stuttgart (Germany), 2004, pp. 29-32] describes several examples showing that a conformation change can produce new hindrance resulting in a modification of the regioselectivity or the stereospecificity, but to the best of our knowledge this is the first example of the new concept of protection.
  • 36
    • 54349127078 scopus 로고    scopus 로고
    • Personal communication
    • Personal communication.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.