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Volumn 61, Issue 26, 1996, Pages 9309-9322

Synthesis of modified carboxyl binding pockets of vancomycin and teicoplanin

Author keywords

[No Author keywords available]

Indexed keywords

MACROLIDE; TEICOPLANIN DERIVATIVE; VANCOMYCIN DERIVATIVE;

EID: 0030448553     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961412m     Document Type: Article
Times cited : (61)

References (80)
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    • Synthesis of 16-membered vancomycin models via macrolactamization, see: (a) Mann, M. J.; Pant, N.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1986, 158-160. (b) Pant, N.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 2002-2003. (c) Crimmin, M. J.; Brown, A. J. Tetrahedron Lett. 1990, 31, 2021-2024. (d) Stone, M. J.; Van Dyk, M. S.; Booth, P. M.; Williams, D. H. J. Chem. Soc., Perkin Trans. I 1991, 1629-1635. (e) Pearson, A. J.; Park, J. G. J. Org. Chem. 1992, 57, 1744-1752. (f) Pearson, A. J.; Lee, K. J. Org. Chem. 1995, 60, 7153-7160.
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    • Synthesis of 16-membered vancomycin models via macrolactamization, see: (a) Mann, M. J.; Pant, N.; Hamilton, A. D. J. Chem. Soc., Chem. Commun. 1986, 158-160. (b) Pant, N.; Hamilton, A. D. J. Am. Chem. Soc. 1988, 110, 2002-2003. (c) Crimmin, M. J.; Brown, A. J. Tetrahedron Lett. 1990, 31, 2021-2024. (d) Stone, M. J.; Van Dyk, M. S.; Booth, P. M.; Williams, D. H. J. Chem. Soc., Perkin Trans. I 1991, 1629-1635. (e) Pearson, A. J.; Park, J. G. J. Org. Chem. 1992, 57, 1744-1752. (f) Pearson, A. J.; Lee, K. J. Org. Chem. 1995, 60, 7153-7160.
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    • For recent books and reviews, see: (a) Terrier, F. Nucleophilic Aromatic Displacement: The Role of the Nitro Group; VCH: New York, 1991; Chapter 1. (b) Paradisi, C. Arene Substitution via Nucleophilic Addition to Electron Deficient Arenes. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 4, pp 423-450. (c) Vlasov, V. M. J. Fluorine Chem. 1993, 61, 193-216.
    • (1991) Nucleophilic Aromatic Displacement: The Role of the Nitro Group
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    • For recent books and reviews, see: (a) Terrier, F. Nucleophilic Aromatic Displacement: The Role of the Nitro Group; VCH: New York, 1991; Chapter 1. (b) Paradisi, C. Arene Substitution via Nucleophilic Addition to Electron Deficient Arenes. Comprehensive Organic Synthesis; Pergamon Press: Oxford, 1991; Vol. 4, pp 423-450. (c) Vlasov, V. M. J. Fluorine Chem. 1993, 61, 193-216.
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    • Preliminary results concerning the synthesis of 3 and 4 have been published: (a) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J. P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784. (b) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787-8790. The M configuration of the atropstereocenter for these macrocycles has been erroneously assigned.
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    • Bois-Choussy, M.1    Beugelmans, R.2    Bouillon, J.P.3    Zhu, J.4
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    • Preliminary results concerning the synthesis of 3 and 4 have been published: (a) Bois-Choussy, M.; Beugelmans, R.; Bouillon, J. P.; Zhu, J. Tetrahedron Lett. 1995, 36, 4781-4784. (b) Beugelmans, R.; Neuville, L.; Bois-Choussy, M.; Zhu, J. Tetrahedron Lett. 1995, 36, 8787-8790. The M configuration of the atropstereocenter for these macrocycles has been erroneously assigned.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8787-8790
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    • note
    • 2O), it is also possible, as suggested by a referee that byproduct 18 could directly result from compound 12 before hydrolysis.
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    • note
    • Decomposition was observed during the hydrolysis of 34 and (4R)-3-[2-[3,5-bis(isopropyloxy)-4-methoxyphenyl]-1-oxoethyl]-4-(phenylmethyl)- 2-oxazolidinone.
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    • note
    • Abbreviations used: DPPA, diphenylphosporyl azide; TFA, trifluoroacetic acid; DCC, 1,3-dicyclohexylcarbodiimide; EDC, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride; HOBt, 1-hydroxybenzotriazole hydrate.
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    • John Wiley & Sons Inc.: New York, Chapter 14
    • The configuration (P or M) of the atropisomer was determined by viewing the atropisomer as helix: "For this designation, only the ligands of highest priority in front and in the back of the framework are considered. If the turn from the priority front ligand to the priority rear ligand is clockwise, the configuration is P, if counterclockwise it is M". See: Eliel, E. L.; Willen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons Inc.: New York, 1994; Chapter 14.
    • (1994) Stereochemistry of Organic Compounds
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    • For a brief discussion concerning negative NOE effects, see ref 1a
    • For a brief discussion concerning negative NOE effects, see ref 1a.
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    • note
    • 3-DMSO. None of these gave satisfactory results.
  • 77
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    • Five thousand conformations of the precursor 45a and macrocyclic product 46a were generated by a random search Monte Carlo method and optimized by molecular mechanics minimization using the Macromodel (Version 3.5) program with the AMBER hydrocarbon force field. From these 5000 conformations, only the conformations with energy values within 3.0 kcal/mol compared to the most stable conformation were analyzed. AMBER generated geometries served as starting points for calculating heats of formation with the help of the MOPAC program (Version 5.0) using semiempirical AM1/RHF parameters (Dewar, M. J. S.; Zoebisch, E. G.; Healy, E. F.; Stewart, J. P. J. Am. Chem. Soc. 1985, 107, 3902-3909). The AM1 calculated heats of formation of the two lowest energy conformers 45a-P (P configuration)-and 45a-M (M configuration) which have very similar geometrical features to those of the two atropisomers 46a-P (P configuration) and 46a-M (M configuration) were found to be -244.04 and -241.42 kcal/mol, respectively. The torsional angles around the C14-C15 and C15-C16 bonds of 45a-P are -73°52 and -76°35 while those of 45a-M are -49°17 and -62°27, respectively. The reduced torsional angles found in the latter create severe steric interactions in the E ring between the methyl hydrogen of the Ala moiety and C19 and between NH12 and C17. These unfavorable interactions may explain the greater heat of formation of 45a-M compared to 45a-P and suggest the predominant formation of 46a-P.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 3902-3909
    • Dewar, M.J.S.1    Zoebisch, E.G.2    Healy, E.F.3    Stewart, J.P.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.