H6515

L-Homoserine

Name: <SC>L</SC>-Homoserine
Brand: SIGMA

Synonym(s):

(S)-2-Amino-4-hydroxybutyric acid, Hse

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About This Item

Linear Formula:

HOCH₂CH₂CH(NH₂)CO₂H

CAS Number:

672-15-1

Molecular Weight:

119.12

NACRES:

NA.26

PubChem Substance ID:

24895748

eCl@ss:

32160406

UNSPSC Code:

12352209

EC Number:

211-590-6

MDL number:

MFCD00063090

Beilstein/REAXYS Number:

1721681

Key Documents

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SMILES string

N[C@@H](CCO)C(O)=O

InChI

1S/C4H9NO3/c5-3(1-2-6)4(7)8/h3,6H,1-2,5H2,(H,7,8)/t3-/m0/s1

InChI key

UKAUYVFTDYCKQA-VKHMYHEASA-N

assay

≥98% (TLC)

form

powder

color

white to off-white

mp

203 °C (dec.) (lit.)

application(s)

cell analysis
detection

Quality Level

100

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Amino Acids

Biochemicals

Cell Culture Supplements & Reagents

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Show Differences

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This Item	69453	O9014	T8441
Sigma-Aldrich H6515 L-Homoserine	Sigma-Aldrich 69453 L-Homocysteine	Sigma-Aldrich O9014 N-(3-Oxodecanoyl)-L-homoserine lactone	Sigma-Aldrich T8441 L-Threonine
form powder	form powder	form powder	form powder
assay ≥98% (TLC)	assay ≥98.0% (NT)	assay ≥98% (TLC)	assay 99.0-101.0%
Quality Level 100	Quality Level 100	Quality Level 200	Quality Level 300
color white to off-white	color white	color white	color white
mp 203 °C (dec.) (lit.)	mp 263-265 °C	mp -	mp 256 °C (dec.) (lit.)
application(s) cell analysis detection	application(s) cell analysis	application(s) cell analysis	application(s) pharmaceutical (small molecule)

Application

L-Homoserine has been used as an internal standard for neurotransmitter analysis[1] and amino acids quantification.[2]

Biochem/physiol Actions

L-Homoserine is synthesized by deoxidation process, catalysed by homoserine dehydrogenase. This is one of the steps in the synthesis of L-threonine. The carbon flux in in bacteria such as E. coli is maintained by this reaction.[3]

L-Homoserine is used in the biosynthesis of methionine, threonine and isoleucine.

General description

L-Homoserine is a variant of serine with an additional carbon on its side chain.[4]

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Neurotoxic effect of maneb in rats as studied by neurochemical and immunohistochemical parameters

Nielsen BS, et al.

Environmental Toxicology and Pharmacology, 21(3), 268-275 (2006)

Reprogramming Microbial Metabolic Pathways, 288-288 (2012)

Chiral recognition of non-natural ?-amino acids

Gal JF, et al.

International Journal of Mass Spectrometry, 222(1?3), 259-267 (2003)

Quorum-sensing systems LuxS/autoinducer 2 and Com regulate Streptococcus pneumoniae biofilms in a bioreactor with living cultures of human respiratory cells.

Jorge E Vidal et al.

Infection and immunity, 81(4), 1341-1353 (2013-02-14)

Streptococcus pneumoniae forms organized biofilms in the human upper respiratory tract that may play an essential role in both persistence and acute respiratory infection. However, the production and regulation of biofilms on human cells is not yet fully understood. In

Active efflux influences the potency of quorum sensing inhibitors in Pseudomonas aeruginosa.

Joseph D Moore et al.

Chembiochem : a European journal of chemical biology, 15(3), 435-442 (2014-01-31)

Many bacteria regulate gene expression through a cell-cell signaling process called quorum sensing (QS). In proteobacteria, QS is largely mediated by signaling molecules known as N-acylated L-homoserine lactones (AHLs) and their associated intracellular LuxR-type receptors. The design of non-native small

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