An Isofagomine Analogue with an Amidine at the Pseudoanomeric Position

Emil Lindbäck; Óscar López; José G. Fernández-Bolaños; Stephan P. A. Sauer; Mikael Bols

doi:10.1021/ol200942g

An Isofagomine Analogue with an Amidine at the Pseudoanomeric Position

Emil Lindbäck, Óscar López, José G. Fernández-Bolaños, Stephan P. A. Sauer, Mikael Bols

Department of Chemistry

13 Citations (Scopus)

Abstract

(3R,4R,5R)-2-Imino-3,4-dihydroxy-5-hydroxymethylpiperidine hydrocloride or isofagomidine was synthesized from d-arabinose in 12 steps and an overall yield of 9.9%. The synthesis proceeded by introduction of an aminomethyl group in the 4-position of d-arabinose and conversion of C-1 into a nitrile. The key step in the synthesis was a copper-catalyzed cyclization of aminonitrile to amidine. Isofagomidine was a potent α-mannosidase inhibitor (K_i = 0.75 μM).

Original language	English
Journal	Organic Letters
Volume	13
Issue number	11
Pages (from-to)	2908-2911
ISSN	1523-7060
DOIs	https://doi.org/10.1021/ol200942g
Publication status	Published - 3 Jun 2011

Keywords

Faculty of Science
Chemistry

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title = "An Isofagomine Analogue with an Amidine at the Pseudoanomeric Position",

abstract = "(3R,4R,5R)-2-Imino-3,4-dihydroxy-5-hydroxymethylpiperidine hydrocloride or isofagomidine was synthesized from d-arabinose in 12 steps and an overall yield of 9.9%. The synthesis proceeded by introduction of an aminomethyl group in the 4-position of d-arabinose and conversion of C-1 into a nitrile. The key step in the synthesis was a copper-catalyzed cyclization of aminonitrile to amidine. Isofagomidine was a potent α-mannosidase inhibitor (Ki = 0.75 μM).",

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author = "Emil Lindb{\"a}ck and {\'O}scar L{\'o}pez and Fern{\'a}ndez-Bola{\~n}os, {Jos{\'e} G.} and Sauer, {Stephan P. A.} and Mikael Bols",

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doi = "10.1021/ol200942g",

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T1 - An Isofagomine Analogue with an Amidine at the Pseudoanomeric Position

AU - Lindbäck, Emil

AU - López, Óscar

AU - Fernández-Bolaños, José G.

AU - Sauer, Stephan P. A.

AU - Bols, Mikael

PY - 2011/6/3

Y1 - 2011/6/3

N2 - (3R,4R,5R)-2-Imino-3,4-dihydroxy-5-hydroxymethylpiperidine hydrocloride or isofagomidine was synthesized from d-arabinose in 12 steps and an overall yield of 9.9%. The synthesis proceeded by introduction of an aminomethyl group in the 4-position of d-arabinose and conversion of C-1 into a nitrile. The key step in the synthesis was a copper-catalyzed cyclization of aminonitrile to amidine. Isofagomidine was a potent α-mannosidase inhibitor (Ki = 0.75 μM).

AB - (3R,4R,5R)-2-Imino-3,4-dihydroxy-5-hydroxymethylpiperidine hydrocloride or isofagomidine was synthesized from d-arabinose in 12 steps and an overall yield of 9.9%. The synthesis proceeded by introduction of an aminomethyl group in the 4-position of d-arabinose and conversion of C-1 into a nitrile. The key step in the synthesis was a copper-catalyzed cyclization of aminonitrile to amidine. Isofagomidine was a potent α-mannosidase inhibitor (Ki = 0.75 μM).

KW - Faculty of Science

KW - Chemistry

U2 - 10.1021/ol200942g

DO - 10.1021/ol200942g

M3 - Journal article

C2 - 21548609

SN - 1523-7060

VL - 13

SP - 2908

EP - 2911

JO - Organic Letters

JF - Organic Letters

IS - 11

ER -

An Isofagomine Analogue with an Amidine at the Pseudoanomeric Position

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