Cyclic guanidine containing amino acids that promote glucocerebrosidase

Zahraa S. Al-Taie; Barbara Bartholomew; Simon J. Coles; Daniel M. Evans; Jackie Hollinshead; Leigh F. Jones; Rolf Kraehenbuehl; Patrick J. Murphy; Robert J. Nash; Yana B. Penkova; Graham J. Tizzard

doi:10.1016/j.tet.2022.132959

Cyclic guanidine containing amino acids that promote glucocerebrosidase

Zahraa S. Al-Taie, Barbara Bartholomew, Simon J. Coles, Daniel M. Evans, Jackie Hollinshead, Leigh F. Jones, Rolf Kraehenbuehl, Patrick J. Murphy, Robert J. Nash, Yana B. Penkova, Graham J. Tizzard

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

Abstract

Novel cyclic guanidine containing amino acids (S)-1, 2 and 3 were prepared from l-serine 5. (S)-2-Imino-3-methylimidazolidine-4-carboxylic acid hydrochloride salt 2. HCl and (3S, 6S)-3,6-bis(hydroxymethyl)-1,4-dimethylpiperazine-2,5-dione 15 showed in vitro promotion of the enzyme glucocerebrosidase.

Original language	English
Article number	132959
Journal	Tetrahedron
Volume	123
DOIs	https://doi.org/10.1016/j.tet.2022.132959
Publication status	Published - 24 Sept 2022
Externally published	Yes

Keywords

Cyclic guanidines
Glycosidase inhibitors
Glycosidase promoters
KBURPLQLJFTMFQ-FQDRLZKGSA-N
LRJQFCYXGYOOTO-UHFFFAOYSA-M
N-methylation
RZYQDFCBVBWREJ-DJHGXJLXSA-N
VUCYZAXAFHYSIY-KIFWWAFVSA-N

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title = "Cyclic guanidine containing amino acids that promote glucocerebrosidase",

abstract = "Novel cyclic guanidine containing amino acids (S)-1, 2 and 3 were prepared from l-serine 5. (S)-2-Imino-3-methylimidazolidine-4-carboxylic acid hydrochloride salt 2. HCl and (3S, 6S)-3,6-bis(hydroxymethyl)-1,4-dimethylpiperazine-2,5-dione 15 showed in vitro promotion of the enzyme glucocerebrosidase.",

keywords = "Cyclic guanidines, Glycosidase inhibitors, Glycosidase promoters, KBURPLQLJFTMFQ-FQDRLZKGSA-N, LRJQFCYXGYOOTO-UHFFFAOYSA-M, N-methylation, RZYQDFCBVBWREJ-DJHGXJLXSA-N, VUCYZAXAFHYSIY-KIFWWAFVSA-N",

author = "Al-Taie, {Zahraa S.} and Barbara Bartholomew and Coles, {Simon J.} and Evans, {Daniel M.} and Jackie Hollinshead and Jones, {Leigh F.} and Rolf Kraehenbuehl and Murphy, {Patrick J.} and Nash, {Robert J.} and Penkova, {Yana B.} and Tizzard, {Graham J.}",

note = "Funding Information: The authors would like to thank the Iraqi government (ZSA-T) and acknowledge the support of the Centre for Environmental Biotechnology Project part-funded by the European Regional Development Fund (ERDF) through the Welsh Government. We would like to thank the BEACON II scheme (ERDF; PJM) and the EPSRC National Mass Spectrometry Facility at Swansea. Publisher Copyright: {\textcopyright} 2022 Elsevier Ltd",

year = "2022",

month = sep,

day = "24",

doi = "10.1016/j.tet.2022.132959",

language = "English",

volume = "123",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier",

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TY - JOUR

T1 - Cyclic guanidine containing amino acids that promote glucocerebrosidase

AU - Al-Taie, Zahraa S.

AU - Bartholomew, Barbara

AU - Coles, Simon J.

AU - Evans, Daniel M.

AU - Hollinshead, Jackie

AU - Jones, Leigh F.

AU - Kraehenbuehl, Rolf

AU - Murphy, Patrick J.

AU - Nash, Robert J.

AU - Penkova, Yana B.

AU - Tizzard, Graham J.

N1 - Funding Information: The authors would like to thank the Iraqi government (ZSA-T) and acknowledge the support of the Centre for Environmental Biotechnology Project part-funded by the European Regional Development Fund (ERDF) through the Welsh Government. We would like to thank the BEACON II scheme (ERDF; PJM) and the EPSRC National Mass Spectrometry Facility at Swansea. Publisher Copyright: © 2022 Elsevier Ltd

PY - 2022/9/24

Y1 - 2022/9/24

N2 - Novel cyclic guanidine containing amino acids (S)-1, 2 and 3 were prepared from l-serine 5. (S)-2-Imino-3-methylimidazolidine-4-carboxylic acid hydrochloride salt 2. HCl and (3S, 6S)-3,6-bis(hydroxymethyl)-1,4-dimethylpiperazine-2,5-dione 15 showed in vitro promotion of the enzyme glucocerebrosidase.

AB - Novel cyclic guanidine containing amino acids (S)-1, 2 and 3 were prepared from l-serine 5. (S)-2-Imino-3-methylimidazolidine-4-carboxylic acid hydrochloride salt 2. HCl and (3S, 6S)-3,6-bis(hydroxymethyl)-1,4-dimethylpiperazine-2,5-dione 15 showed in vitro promotion of the enzyme glucocerebrosidase.

KW - Cyclic guanidines

KW - Glycosidase inhibitors

KW - Glycosidase promoters

KW - KBURPLQLJFTMFQ-FQDRLZKGSA-N

KW - LRJQFCYXGYOOTO-UHFFFAOYSA-M

KW - N-methylation

KW - RZYQDFCBVBWREJ-DJHGXJLXSA-N

KW - VUCYZAXAFHYSIY-KIFWWAFVSA-N

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U2 - 10.1016/j.tet.2022.132959

DO - 10.1016/j.tet.2022.132959

M3 - Article

SN - 0040-4020

VL - 123

JO - Tetrahedron

JF - Tetrahedron

M1 - 132959

ER -

Cyclic guanidine containing amino acids that promote glucocerebrosidase

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Keywords

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Corrigendum to “Cyclic guanidine containing amino acids that promote glucocerebrosidase”: [Tetrahedron 123C (2022) 132959]

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