N-Fmoc-protected(α-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation

Alan R. Katritzky; Megumi Yoshioka; Tamari Narindoshvili; Alfred Chung; Niveen M. Khashab

doi:10.1111/j.1747-0285.2008.00689.x

N-Fmoc-protected(α-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation

Alan R. Katritzky, Megumi Yoshioka, Tamari Narindoshvili, Alfred Chung, Niveen M. Khashab

Research output: Contribution to journal › Article › peer-review

17 Scopus citations

Abstract

N-Fmoc-protected(α-aminoacyl)benzotriazoles 1a-d readily afford chiral N-Fmoc-protected-α-dipeptides 2a-f (77-89%). Compounds 2a-f are further converted into N-Fmoc-protected(α-dipeptidoyl)benzotriazoles 3a-f (71% average yield). Under mild microwave irradiation, 3a-f are used in solid-phase peptide segment condensation syntheses to give tri-, tetra-, penta-, hexa-, and heptapeptides (20-68%).

Original language	English (US)
Pages (from-to)	182-188
Number of pages	7
Journal	Chemical Biology and Drug Design
Volume	72
Issue number	3
DOIs	https://doi.org/10.1111/j.1747-0285.2008.00689.x
State	Published - Sep 2008
Externally published	Yes

Keywords

Fmoc strategy
Microwave irradiation
N-Fmoc-protected(α-dipeptidoyl) benzotriazoles
Segment condensation
Solid-phase peptide synthesis

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Pharmacology
Drug Discovery
Organic Chemistry

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Cite this

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title = "N-Fmoc-protected(α-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation",

abstract = "N-Fmoc-protected(α-aminoacyl)benzotriazoles 1a-d readily afford chiral N-Fmoc-protected-α-dipeptides 2a-f (77-89%). Compounds 2a-f are further converted into N-Fmoc-protected(α-dipeptidoyl)benzotriazoles 3a-f (71% average yield). Under mild microwave irradiation, 3a-f are used in solid-phase peptide segment condensation syntheses to give tri-, tetra-, penta-, hexa-, and heptapeptides (20-68%).",

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language = "English (US)",

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journal = "Chemical Biology and Drug Design",

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T1 - N-Fmoc-protected(α-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation

AU - Katritzky, Alan R.

AU - Yoshioka, Megumi

AU - Narindoshvili, Tamari

AU - Chung, Alfred

AU - Khashab, Niveen M.

PY - 2008/9

Y1 - 2008/9

N2 - N-Fmoc-protected(α-aminoacyl)benzotriazoles 1a-d readily afford chiral N-Fmoc-protected-α-dipeptides 2a-f (77-89%). Compounds 2a-f are further converted into N-Fmoc-protected(α-dipeptidoyl)benzotriazoles 3a-f (71% average yield). Under mild microwave irradiation, 3a-f are used in solid-phase peptide segment condensation syntheses to give tri-, tetra-, penta-, hexa-, and heptapeptides (20-68%).

AB - N-Fmoc-protected(α-aminoacyl)benzotriazoles 1a-d readily afford chiral N-Fmoc-protected-α-dipeptides 2a-f (77-89%). Compounds 2a-f are further converted into N-Fmoc-protected(α-dipeptidoyl)benzotriazoles 3a-f (71% average yield). Under mild microwave irradiation, 3a-f are used in solid-phase peptide segment condensation syntheses to give tri-, tetra-, penta-, hexa-, and heptapeptides (20-68%).

KW - Fmoc strategy

KW - Microwave irradiation

KW - N-Fmoc-protected(α-dipeptidoyl) benzotriazoles

KW - Segment condensation

KW - Solid-phase peptide synthesis

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U2 - 10.1111/j.1747-0285.2008.00689.x

DO - 10.1111/j.1747-0285.2008.00689.x

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N-Fmoc-protected(α-dipeptidoyl)benzotriazoles for efficient solid-phase peptide synthesis by segment condensation

Abstract

Keywords

ASJC Scopus subject areas

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