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^*

^*Corresponding author for this work

Hospital Pharmacy

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

28 Scopus citations

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
State	Published - 2010/04/28

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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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{d2f2814a954d465aa31179f4215e7d98,

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.}",

note = "Funding Information: Support from a Nuffield Foundation Undergraduate Research Bursary [to P.C.] and Summit plc is gratefully acknowledged.",

year = "2010",

month = apr,

day = "28",

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

language = "英語",

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.

N1 - Funding Information: Support from a Nuffield Foundation Undergraduate Research Bursary [to P.C.] and Summit plc is gratefully acknowledged.

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 - http://www.scopus.com/inward/record.url?scp=77949568804&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2010.02.063

DO - 10.1016/j.tetlet.2010.02.063

M3 - 学術論文

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

ASJC Scopus subject areas

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