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Volumn 129, Issue 40, 2007, Pages 12222-12231

Simultaneous arming and structure/activity studies of natural products employing O-H insertions: An expedient and versatile strategy for natural products-based chemical genetics

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL GENETICS; MONOFUNCTIONALIZATION; NATURAL PRODUCTS;

EID: 35048856423     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0733686     Document Type: Article
Times cited : (78)

References (91)
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    • The term chemoselectivity is used to describe reactions that discriminate between two functional group types in a given molecule. Site selectivity has been utilized to describe selective reaction at one position in a natural product (see ref 11) or one amino acid of a protein over another but it does not inherently imply chemoselective. Therefore, we propose use of the term chemosite selective to describe a reaction that exhibits both chemo and site selectivity
    • The term chemoselectivity is used to describe reactions that discriminate between two functional group types in a given molecule. Site selectivity has been utilized to describe selective reaction at one position in a natural product (see ref 11) or one amino acid of a protein over another but it does not inherently imply chemoselective. Therefore, we propose use of the term "chemosite selective" to describe a reaction that exhibits both chemo and site selectivity.
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    • For a recent example of minimal peptide-mediated acylation of erythromycin aglycone, see: a
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    • This article, which appeared when our work was in progress, adequately describes the concept of double diastereodifferentiation employing chiral peptide catalysts and natural products. For examples of glycorandomization of natural products, see: (b) Thibodeaux, C. J, Melancon, C. E, Liu, H.-W. Nature 2007, 446, 1008-1016
    • This article, which appeared when our work was in progress, adequately describes the concept of "double diastereodifferentiation" employing chiral peptide catalysts and natural products. For examples of glycorandomization of natural products, see: (b) Thibodeaux, C. J.; Melancon, C. E.; Liu, H.-W. Nature 2007, 446, 1008-1016.
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    • For examples of prenylation of natural products, see: (g) Kuzuyama, T, Noel, J. P, Richard, S. B. Nature 2005, 435, 983-987
    • For examples of prenylation of natural products, see: (g) Kuzuyama, T.; Noel, J. P.; Richard, S. B. Nature 2005, 435, 983-987.
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    • For some representative mild methods for derivatization of alcohols in natural products, see: a
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    • For details regarding the preparation of alkynyl diazo esters utilized in this study, see Supporting Information
    • For details regarding the preparation of alkynyl diazo esters utilized in this study, see Supporting Information.
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    • For an excellent review on donor- and acceptor-substituted carbenoids, see
    • For an excellent review on donor- and acceptor-substituted carbenoids, see: Davies, H. M. L.; Nikolai, J. Org. Biomol. Chem. 2005, 3, 4176-4187.
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    • Hydrolysis experiments were performed with a simple model ester i to determine the stability of the bromobenzyl acetate esters. Complete hydrolysis of ester i required a pH = 13 at 22°C in 48 h and delivered the bromobenzylacetic acid ii. See Supporting Information for details. (Chemical Equation Presented)
    • Hydrolysis experiments were performed with a simple model ester i to determine the stability of the bromobenzyl acetate esters. Complete hydrolysis of ester i required a pH = 13 at 22°C in 48 h and delivered the bromobenzylacetic acid ii. See Supporting Information for details. (Chemical Equation Presented)
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    • See Supporting Information for details
    • See Supporting Information for details.
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    • Employing Affigel, see: (b) Reference 35b.
    • Employing Affigel, see: (b) Reference 35b.
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    • By the yeast three-hybrid system using an FK506-biotin conjugate, see: (d) de Felipe, K.; Carter, B. T.; Althoff, E. A.; Cornish, V. W. Biochemistry 2004, 43, 10353-10363.
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    • While our work was in progress, a similar observation using a hydrophilic polymer-immobilized FK506 was reported. See: Takahashi, T, Shiyama, T, Mori, T, Hosoya, K, Tanaka, A. Anal. Bioanal. Chem. 2006, 385, 122-127
    • While our work was in progress, a similar observation using a hydrophilic polymer-immobilized FK506 was reported. See: Takahashi, T.; Shiyama, T.; Mori, T.; Hosoya, K.; Tanaka, A. Anal. Bioanal. Chem. 2006, 385, 122-127.
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    • The cyclopentyl alcohol (C13) has previously been shown to be the most readily functionalized. See ref 32
    • The cyclopentyl alcohol (C13) has previously been shown to be the most readily functionalized. See ref 32.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.