Synthetic studies towards glycopeptide antibiotics: Synthesis of the 16-membered cyclic tripeptide (DOEG ring) system of teicoplanin

Rao, A. V. Rama; Reddy, K. Laxma; Vittal, T. V. S. K.; Reddy, M. M.; Pathi, P. L.

doi:10.1016/0040-4039(96)00459-5

Cited by 14 publications

(2 citation statements)

References 13 publications

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“…The presence of the additional fourth ring, formed by the first and third amino acids, considerably complicates the synthesis. At the initial stages of researches in this region only small fragments of the molecule were obtained, close in structure to K-13 [18,35] or to the fragment M(1-O-3)(4-O-6) of natural antibiotics [36].…”

Section: Synthesis Of the Tricyclic Fragment M(1-o-3)(2-o-4)(4-o-6) Omentioning

confidence: 99%

Antibacterial glycopeptide antibiotics (review)

Preobrazhenskaya¹,

Miroshnikova²,

Pavlov³

et al. 1998

Chem Heterocycl Compd

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Section: Synthesis Of the Tricyclic Fragment M(1-o-3)(2-o-4)(4-o-6) Omentioning

confidence: 99%

Antibacterial glycopeptide antibiotics (review)

Preobrazhenskaya¹,

Miroshnikova²,

Pavlov³

et al. 1998

Chem Heterocycl Compd

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“…This method has been successfully applied to the synthesis of the naturally occurring 17-membered cyclic tripeptide K-13, 16-membered vancomycin models, 14-membered teicoplanin, and bouvardin models . Shortly after the disclosure of our work, other groups, notably, those of Rama Rao, Boger, Rich,18a Pearson,18b and very recently Evans, have employed this methodology in the realization of their synthetic strategies.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Modified Carboxyl Binding Pockets of Vancomycin and Teicoplanin

et al. 1996

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Sixteen-membered macrocycle 3 and 16+14 bicyclic compound 4, incorporating a terminal primary hydroxyl group in the peptide sequence, have been designed and synthesized. The syntheses feature the use of an efficient cycloetherification based on an intramolecular SNAr reaction for the formation of biaryl ether bonds. Cyclization of linear tetrapeptide 30, prepared via a convergent [2+2] segment coupling between 26 and 29, gave macrocycle 31 (P configuration) as a single isolable atropisomer. Removal of the Boc protecting group afforded the modified carboxyl binding pocket of vancomycin 3. A sequential 2-fold intramolecular SNAr reaction has been used to construct the model bicyclic system (i.e. 4) of the D-O-E-F-O-G ring of teicoplanin. Cyclization conditions (CsF, DMF, room temperature) are sufficiently mild that the configuration of the racemization-prone arylglycine residue was not affected. Chiral building blocks such as d-(1R)-[2-[(tert-butyldimethylsilyl)oxy]-1-[3-(allyloxy)phenyl]ethyl]amine 16, and l-(S)-N-Boc-[3-(isopropyloxy)phenyl]glycine (32) were synthesized employing Evans' asymmetric azidation method, while l-(S)-4-fluoro-3-nitrophenylalanine methyl ester 23 was prepared using Schöllkopf's bislactim ether as chiral glycine template. Compound 3 showed interesting conformational properties compared to vancomycin and its binding with Ac-d-Ala was studied by NMR titration experiments. A dissociation constant (K d = 5 × 10-4) was calculated by a curve fitting method. Compound 4 is currently the most advanced synthetic intermediate toward the total synthesis of teicoplanin.

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6.1 C–C Bond Formation: Alkylation

Uraguchi

Ooi

2012

Comprehensive Chirality

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Synthetic studies towards glycopeptide antibiotics: Synthesis of the 16-membered cyclic tripeptide (DOEG ring) system of teicoplanin

Cited by 14 publications

References 13 publications

Antibacterial glycopeptide antibiotics (review)

Antibacterial glycopeptide antibiotics (review)

Synthesis of Modified Carboxyl Binding Pockets of Vancomycin and Teicoplanin

6.1 C–C Bond Formation: Alkylation

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