Synthesis of 2-acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc] from d-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases

Daniel Best; Phoom Chairatana; Andreas F.G. Glawar; Elizabeth Crabtree; Terry D. Butters; Francis X. Wilson; Chu Yi Yu; Wu Bao Wang; Yue Mei Jia; Isao Adachi; Atsushi Kato; George W.J. Fleet

doi:10.1016/j.tetlet.2010.02.063

Synthesis of 2-acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc] from d-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases

Daniel Best
, Phoom Chairatana
, Andreas F.G. Glawar
, Elizabeth Crabtree
, Terry D. Butters
, Francis X. Wilson
, Chu Yi Yu
, Wu Bao Wang
, Yue Mei Jia
, Isao Adachi
, Atsushi Kato
, George W.J. Fleet

Oxford University Clinical Academic Graduate School
University of Oxford Medical Sciences Division
Summit PLC
Institute of Chemistry Chinese Academy of Sciences
Toyama Medical and Pharmaceutical University

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

28 Citations (Scopus)

Abstract

2-Acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc], prepared in 20% overall yield from d-glucuronolactone, is the first potent competitive sub-micromolar inhibitor of α-N-acetyl-galactosaminidases (K_i 0.081 μM from chicken liver, K_i 0.136 μM from Charonia lampas). DGJNAc is a good competitive-whereas the enantiomer l-DGJNAc is a very weak but non-competitive-inhibitor of β-hexosaminidases.

Original language	English
Pages (from-to)	2222-2224
Number of pages	3
Journal	Tetrahedron Letters
Volume	51
Issue number	17
DOIs	https://doi.org/10.1016/j.tetlet.2010.02.063
Publication status	Published - 28 Apr 2010
Externally published	Yes

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Best, D., Chairatana, P., Glawar, A. F. G., Crabtree, E., Butters, T. D., Wilson, F. X., Yu, C. Y., Wang, W. B., Jia, Y. M., Adachi, I., Kato, A., & Fleet, G. W. J. (2010). Synthesis of 2-acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc] from d-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases. Tetrahedron Letters, 51(17), 2222-2224. https://doi.org/10.1016/j.tetlet.2010.02.063

@article{67d26dfb253548ea974503032fbea2a4,

title = "Synthesis of 2-acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc] from d-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases",

abstract = "2-Acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc], prepared in 20\% overall yield from d-glucuronolactone, is the first potent competitive sub-micromolar inhibitor of α-N-acetyl-galactosaminidases (Ki 0.081 μM from chicken liver, Ki 0.136 μM from Charonia lampas). DGJNAc is a good competitive-whereas the enantiomer l-DGJNAc is a very weak but non-competitive-inhibitor of β-hexosaminidases.",

author = "Daniel Best and Phoom Chairatana and Glawar, \{Andreas F.G.\} and Elizabeth Crabtree and Butters, \{Terry D.\} and Wilson, \{Francis X.\} and Yu, \{Chu Yi\} and Wang, \{Wu Bao\} and Jia, \{Yue Mei\} and Isao Adachi and Atsushi Kato and Fleet, \{George W.J.\}",

year = "2010",

month = apr,

day = "28",

doi = "10.1016/j.tetlet.2010.02.063",

language = "English",

volume = "51",

pages = "2222--2224",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd.",

number = "17",

}

Best, D, Chairatana, P, Glawar, AFG, Crabtree, E, Butters, TD, Wilson, FX, Yu, CY, Wang, WB, Jia, YM, Adachi, I, Kato, A & Fleet, GWJ 2010, 'Synthesis of 2-acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc] from d-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases', Tetrahedron Letters, vol. 51, no. 17, pp. 2222-2224. https://doi.org/10.1016/j.tetlet.2010.02.063

TY - JOUR

T1 - Synthesis of 2-acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc] from d-glucuronolactone

T2 - the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases

AU - Best, Daniel

AU - Chairatana, Phoom

AU - Glawar, Andreas F.G.

AU - Crabtree, Elizabeth

AU - Butters, Terry D.

AU - Wilson, Francis X.

AU - Yu, Chu Yi

AU - Wang, Wu Bao

AU - Jia, Yue Mei

AU - Adachi, Isao

AU - Kato, Atsushi

AU - Fleet, George W.J.

PY - 2010/4/28

Y1 - 2010/4/28

N2 - 2-Acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc], prepared in 20% overall yield from d-glucuronolactone, is the first potent competitive sub-micromolar inhibitor of α-N-acetyl-galactosaminidases (Ki 0.081 μM from chicken liver, Ki 0.136 μM from Charonia lampas). DGJNAc is a good competitive-whereas the enantiomer l-DGJNAc is a very weak but non-competitive-inhibitor of β-hexosaminidases.

AB - 2-Acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc], prepared in 20% overall yield from d-glucuronolactone, is the first potent competitive sub-micromolar inhibitor of α-N-acetyl-galactosaminidases (Ki 0.081 μM from chicken liver, Ki 0.136 μM from Charonia lampas). DGJNAc is a good competitive-whereas the enantiomer l-DGJNAc is a very weak but non-competitive-inhibitor of β-hexosaminidases.

UR - https://www.scopus.com/pages/publications/77949568804

U2 - 10.1016/j.tetlet.2010.02.063

DO - 10.1016/j.tetlet.2010.02.063

M3 - Article

AN - SCOPUS:77949568804

SN - 0040-4039

VL - 51

SP - 2222

EP - 2224

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 17

ER -

Synthesis of 2-acetamido-1,2-dideoxy-d-galacto-nojirimycin [DGJNAc] from d-glucuronolactone: the first sub-micromolar inhibitor of α-N-acetylgalactosaminidases

Abstract

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