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Volumn 3, Issue 4, 2008, Pages 619-626

Total synthesis and initial structure-activity relationships of longicatenamycin A

Author keywords

Antibiotics; Cyclization; Cyclopeptides; Gram positive bacteria; Structure activity relationships

Indexed keywords

ANTIINFECTIVE AGENT; LONGICATENAMYCIN; PEPTIDE;

EID: 47249135432     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200700297     Document Type: Conference Paper
Times cited : (23)

References (92)
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    • Attempts to selectively hydrolyze the C-terminal D-Orn methyl ester prior to cyclization exclusively yielded the undesired diacid (37→38). To solve this problem, we installed a trimethylsilylethyl (TMSE) ester as an (Chemical Equation Presented) additional dimension of protection at the D-Orn carboxylate. Boc deprotection had to be carried out cautiously due to the acid sensitivity of the TMSE group; now the complete N-deprotection of the indole ring could no longer be achieved with HCl (24→39). Still, the cyclization sequence could be done with the mono-Boc/bis-Boc mixture (40→32). (Chemical Equation Presented)
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    • [7] hydrolyzed the S-520 complex with 6N HCl at 105°C. Under these conditions, HyGln would have been transformed into HyGlu, the amino acid detected in the hydrolysate.
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    • 20=+13.2° (c=0.46, MeOH) [would correspond to +12.1° for the TFA salt].
    • 20=+13.2° (c=0.46, MeOH) [would correspond to +12.1° for the TFA salt].
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.