Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp)

Philip McGurk; Grace X. Chang; Todd L. Lowary; Michael McNeil; Robert A. Field

doi:10.1016/S0040-4039(01)00118-6

Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp)

Philip McGurk
, Grace X. Chang
, Todd L. Lowary
, Michael McNeil
, Robert A. Field

School of Chemistry, Pharmacy and Pharmacology

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

14 Citations (Scopus)

Abstract

The stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro.

Original language	English
Pages (from-to)	2231-2234
Number of pages	4
Journal	Tetrahedron Letters
Volume	42
Issue number	11
Early online date	27 Feb 2001
DOIs	https://doi.org/10.1016/S0040-4039(01)00118-6
Publication status	Published - 11 Mar 2001

Keywords

2,5-anhydro-D-mannitol
Cell wall biosynthesis
D-arabinose
Mycobacteria
Phosphonophosphate

Access to Document

10.1016/S0040-4039(01)00118-6

Cite this

McGurk, P., Chang, G. X., Lowary, T. L., McNeil, M., & Field, R. A. (2001). Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). Tetrahedron Letters, 42(11), 2231-2234. https://doi.org/10.1016/S0040-4039(01)00118-6

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title = "Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp)",

abstract = "The stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro.",

keywords = "2,5-anhydro-D-mannitol, Cell wall biosynthesis, D-arabinose, Mycobacteria, Phosphonophosphate",

author = "Philip McGurk and Chang, \{Grace X.\} and Lowary, \{Todd L.\} and Michael McNeil and Field, \{Robert A.\}",

note = "Funding Information: This work was supported by US NIH/NIAID AIDS-FIRCA grant R03 TW00938-01 and NIH grant AI 33706, the UK BBSRC (studentship to P.McG.) and the Ohio State University. We thank the EPSRC Mass Spectrometry Service at the University of Wales, Swansea for invaluable support. ",

year = "2001",

month = mar,

day = "11",

doi = "10.1016/S0040-4039(01)00118-6",

language = "English",

volume = "42",

pages = "2231--2234",

journal = "Tetrahedron Letters",

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McGurk, P, Chang, GX, Lowary, TL, McNeil, M & Field, RA 2001, 'Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp)', Tetrahedron Letters, vol. 42, no. 11, pp. 2231-2234. https://doi.org/10.1016/S0040-4039(01)00118-6

Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). / McGurk, Philip; Chang, Grace X.; Lowary, Todd L. et al.
In: Tetrahedron Letters, Vol. 42, No. 11, 11.03.2001, p. 2231-2234.

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

TY - JOUR

T1 - Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp)

AU - McGurk, Philip

AU - Chang, Grace X.

AU - Lowary, Todd L.

AU - McNeil, Michael

AU - Field, Robert A.

N1 - Funding Information: This work was supported by US NIH/NIAID AIDS-FIRCA grant R03 TW00938-01 and NIH grant AI 33706, the UK BBSRC (studentship to P.McG.) and the Ohio State University. We thank the EPSRC Mass Spectrometry Service at the University of Wales, Swansea for invaluable support.

PY - 2001/3/11

Y1 - 2001/3/11

N2 - The stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro.

AB - The stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp) from D-glucosamine is described. This compound was evaluated for its ability to serve as a stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp). The phosphonophosphate proved incapable of interfering with formation of the mycobacterial arabinan precursor decaprenylphospho-arabinose (DpA) in vitro.

KW - 2,5-anhydro-D-mannitol

KW - Cell wall biosynthesis

KW - D-arabinose

KW - Mycobacteria

KW - Phosphonophosphate

UR - https://www.scopus.com/pages/publications/0035843442

U2 - 10.1016/S0040-4039(01)00118-6

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M3 - Article

AN - SCOPUS:0035843442

SN - 0040-4039

VL - 42

SP - 2231

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 11

ER -

Stereospecific synthesis of 5-phospho-α-D-arabinosyl-C-phosphonophosphate (pACpp): A stable analogue of the putative mycobacterial cell wall biosynthetic intermediate 5-phospho-D-arabinosyl pyrophosphate (pApp)

Abstract

Keywords

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