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Volumn 128, Issue 9, 2006, Pages 2885-2892

Total synthesis and evaluation of [Ψ[CH2NH]Tpg 4]vancomycin aglycon: Reengineering vancomycin for dual D-Ala-D-Ala and D-Ala-D-Lac binding

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; CARBON; CHEMICAL BONDS; CHEMICAL MODIFICATION; REACTION KINETICS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

EID: 33644932823     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0572912     Document Type: Article
Times cited : (116)

References (58)
  • 13
    • 0034885143 scopus 로고    scopus 로고
    • Efforts to modify the residue 4 carbonyl by selective reaction of the amide linking residues 4 and 5 within vancomycin aglycon derivatives have not yet been successful in our efforts, and we are unaware of any reports of such modifications. Synthetic reviews: (a) Boger, D. L. Med. Res. Rev. 2001, 21, 356.
    • (2001) Med. Res. Rev. , vol.21 , pp. 356
    • Boger, D.L.1
  • 34
    • 33644941034 scopus 로고    scopus 로고
    • note
    • Compound 7 is available in six steps (37% overall) from methyl gallate using three recrystallizations and was scaled to 300 g, ref 6.
  • 35
    • 33644956309 scopus 로고    scopus 로고
    • note
    • Compound 6 is available in five steps (55% overall) from (R)-4-hydroxyphenyl-glycine using two recrystallizations and was scaled to 60 g, ref 7a.
  • 36
    • 33644965777 scopus 로고    scopus 로고
    • note
    • Benzyl ether deprotection at higher temperatures (25 °C) may lead to competitive aryl bromide reduction, although this was observed in appreciable amounts only when excess Raney nickel was employed.
  • 37
    • 33644939186 scopus 로고    scopus 로고
    • note
    • Saponification of 11 was considerably slower than that of 10 and occasionally required additional LiOH for complete conversion to 12, with little effect on the amount of epimer generated in the reaction.
  • 38
    • 33644932759 scopus 로고    scopus 로고
    • note
    • Compound 13 is available in three steps (45% overall) from 4-fluoro-3-nitrobenzaldehyde and was scaled to 30 g, ref 6.
  • 41
    • 33644938211 scopus 로고    scopus 로고
    • note
    • Recent efforts have led to improvements in the vancomycin CD ring closure, and this method was utilized for the preparation of the analogous intermediates bearing a residue 4/5 thioamide. Its use in the preparation of 5 along with additional vancomycin analogues will be disclosed in due time.
  • 42
    • 33644941900 scopus 로고    scopus 로고
    • note
    • Use of Raney nickel for N-Cbz removal was also successful, although lower recoveries (84%) of the product were observed.
  • 43
    • 33644954972 scopus 로고    scopus 로고
    • note
    • 2.
  • 52
    • 33644958368 scopus 로고    scopus 로고
    • note
    • Reduction of the nitro group was sensitive to the choice of solvent in terms of recovery and observance of side products.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.