Synthesis of beta-D-Galp-(1 -> 4)-alpha-D-Manp methanephosphonate, a substrate analogue for the elongating alpha-D-mannosyl phosphate transferase in the Leishmania

Vladimir S.  Borodkin; Michael A. J.  Ferguson; Andrei V.  Nikolaev

doi:10.1016/S0040-4039(01)00961-3

Synthesis of beta-D-Galp-(1 -> 4)-alpha-D-Manp methanephosphonate, a substrate analogue for the elongating alpha-D-mannosyl phosphate transferase in the Leishmania

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Abstract

An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	5305-5308
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	31
DOIs	https://doi.org/10.1016/S0040-4039(01)00961-3
Publication status	Published - 30 Jul 2001

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title = "Synthesis of beta-D-Galp-(1 -> 4)-alpha-D-Manp methanephosphonate, a substrate analogue for the elongating alpha-D-mannosyl phosphate transferase in the Leishmania",

abstract = "An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.",

author = "Borodkin, \{Vladimir S.\} and Ferguson, \{Michael A. J.\} and Nikolaev, \{Andrei V.\}",

year = "2001",

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doi = "10.1016/S0040-4039(01)00961-3",

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pages = "5305--5308",

journal = "Tetrahedron Letters",

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number = "31",

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Synthesis of beta-D-Galp-(1 -> 4)-alpha-D-Manp methanephosphonate, a substrate analogue for the elongating alpha-D-mannosyl phosphate transferase in the Leishmania. / Borodkin, Vladimir S. ; Ferguson, Michael A. J. ; Nikolaev, Andrei V. .
In: Tetrahedron Letters, Vol. 42, No. 31, 30.07.2001, p. 5305-5308.

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

TY - JOUR

T1 - Synthesis of beta-D-Galp-(1 -> 4)-alpha-D-Manp methanephosphonate, a substrate analogue for the elongating alpha-D-mannosyl phosphate transferase in the Leishmania

AU - Borodkin, Vladimir S.

AU - Ferguson, Michael A. J.

AU - Nikolaev, Andrei V.

PY - 2001/7/30

Y1 - 2001/7/30

N2 - An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

AB - An isosteric C-glycoside phosphono analogue of dec-9-enyl beta -D-galactopyranosyl-(1 -->4)-alpha -D-mannopyranosyl phosphate was synthesised and showed high biological activity in the Leishmania MPT assay. A one-step Horner-Emmons/Michael reaction was developed for the stereoselective preparation of cc-D-mannosyl methanephosphonate derivatives. (C) 2001 Elsevier Science Ltd. All rights reserved.

U2 - 10.1016/S0040-4039(01)00961-3

DO - 10.1016/S0040-4039(01)00961-3

M3 - Article

SN - 0040-4039

VL - 42

SP - 5305

EP - 5308

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 31

ER -

Synthesis of beta-D-Galp-(1 -> 4)-alpha-D-Manp methanephosphonate, a substrate analogue for the elongating alpha-D-mannosyl phosphate transferase in the Leishmania

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