Synthesis of (R)- and (S)-2,3-diaminopropyl sulfate: mechanism based inhibition of glutamate 1-semialdehyde aminomutase

K  Khayer; T  Jenn; M  Akhtar; R  John; D  Gani

Synthesis of (R)- and (S)-2,3-diaminopropyl sulfate: mechanism based inhibition of glutamate 1-semialdehyde aminomutase

K Khayer, T Jenn, M Akhtar, R John, D Gani

School of Chemistry

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

Abstract

A short synthesis of each enantiomer of 2,3-diaminopropyl hydrogensulfate is described starting from (2R)- and (2S)-asparagine. The compounds serve as inhibitors for pyridoxal 5'-phosphate-dependent (2S)-glutamate l-semialdehyde aminotransferase, a target for selective herbicides and antibacterial agents on the tetrapyrrole biosynthetic pathway. The (2R)-enantiomer, as predicted, serves as a potent irreversible inactivator. (C) 2000 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	1637-1641
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Publication status	Published - 4 Mar 2000

Keywords

(2R)-SERINE O-SULFATE
SUICIDE INHIBITORS
ACID DECARBOXYLASE
AMINOTRANSFERASE
STEREOCHEMISTRY
ENZYME
AMINOLEVULINATE
(2S)-SERINE
ACTIVATION
COMPLEXES

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Synthesis of (R)- and (S)-2,3-diaminopropyl sulfate: mechanism based inhibition of glutamate 1-semialdehyde aminomutase",

abstract = "A short synthesis of each enantiomer of 2,3-diaminopropyl hydrogensulfate is described starting from (2R)- and (2S)-asparagine. The compounds serve as inhibitors for pyridoxal 5'-phosphate-dependent (2S)-glutamate l-semialdehyde aminotransferase, a target for selective herbicides and antibacterial agents on the tetrapyrrole biosynthetic pathway. The (2R)-enantiomer, as predicted, serves as a potent irreversible inactivator. (C) 2000 Elsevier Science Ltd. All rights reserved.",

keywords = "(2R)-SERINE O-SULFATE, SUICIDE INHIBITORS, ACID DECARBOXYLASE, AMINOTRANSFERASE, STEREOCHEMISTRY, ENZYME, AMINOLEVULINATE, (2S)-SERINE, ACTIVATION, COMPLEXES",

author = "K Khayer and T Jenn and M Akhtar and R John and D Gani",

year = "2000",

month = mar,

day = "4",

language = "English",

volume = "41",

pages = "1637--1641",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "PERGAMON-ELSEVIER SCIENCE LTD",

}

TY - JOUR

T1 - Synthesis of (R)- and (S)-2,3-diaminopropyl sulfate: mechanism based inhibition of glutamate 1-semialdehyde aminomutase

AU - Khayer, K

AU - Jenn, T

AU - Akhtar, M

AU - John, R

AU - Gani, D

PY - 2000/3/4

Y1 - 2000/3/4

N2 - A short synthesis of each enantiomer of 2,3-diaminopropyl hydrogensulfate is described starting from (2R)- and (2S)-asparagine. The compounds serve as inhibitors for pyridoxal 5'-phosphate-dependent (2S)-glutamate l-semialdehyde aminotransferase, a target for selective herbicides and antibacterial agents on the tetrapyrrole biosynthetic pathway. The (2R)-enantiomer, as predicted, serves as a potent irreversible inactivator. (C) 2000 Elsevier Science Ltd. All rights reserved.

AB - A short synthesis of each enantiomer of 2,3-diaminopropyl hydrogensulfate is described starting from (2R)- and (2S)-asparagine. The compounds serve as inhibitors for pyridoxal 5'-phosphate-dependent (2S)-glutamate l-semialdehyde aminotransferase, a target for selective herbicides and antibacterial agents on the tetrapyrrole biosynthetic pathway. The (2R)-enantiomer, as predicted, serves as a potent irreversible inactivator. (C) 2000 Elsevier Science Ltd. All rights reserved.

KW - (2R)-SERINE O-SULFATE

KW - SUICIDE INHIBITORS

KW - ACID DECARBOXYLASE

KW - AMINOTRANSFERASE

KW - STEREOCHEMISTRY

KW - ENZYME

KW - AMINOLEVULINATE

KW - (2S)-SERINE

KW - ACTIVATION

KW - COMPLEXES

M3 - Article

SN - 0040-4039

VL - 41

SP - 1637

EP - 1641

JO - Tetrahedron Letters

JF - Tetrahedron Letters

ER -

Synthesis of (R)- and (S)-2,3-diaminopropyl sulfate: mechanism based inhibition of glutamate 1-semialdehyde aminomutase

Abstract

Keywords

UN SDGs

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