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459224

Sigma-Aldrich

(S)-α-Amino-γ-butyrolactone hydrochloride

97%

Synonym(s):

L-Homoserine lactone hydrochloride, HSI

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About This Item

Empirical Formula (Hill Notation):
C4H7NO2 · HCl
CAS Number:
2185-03-7
Molecular Weight:
137.56
Beilstein/REAXYS Number:
3562187
EC Number:
218-571-1
MDL number:
MFCD00058172
UNSPSC Code:
12352202
PubChem Substance ID:
24869524
NACRES:
NA.22

assay

97%

form

powder or crystals

optical activity

[α]20/D −27.8°, c = 1 in H2O

mp

210-220 °C (dec.) (lit.)

application(s)

peptide synthesis

SMILES string

Cl.N[C@H]1CCOC1=O

InChI

1S/C4H7NO2.ClH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1

InChI key

XBKCXPRYTLOQKS-DFWYDOINSA-N

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Application

(S)-α-Amino-γ-butyrolactone hydrochloride can be used:
  • As a precursor for the preparation of amino-keto-alcohols and β-amino acids.
  • To prepare N-acylhomoserine lactone (AHL) analogs by reacting with substituted 2-chloro-N-phenylacetamide and different halides.
  • As a starting material for the synthesis of L-discadenine.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Design, synthesis and antibacterial evaluation of novel AHL analogues
Ren J, et al.
Bioorganic & Medicinal Chemistry Letters, 23(14), 4154-4156 (2013)
Natural products from social amoebae
Barnett R and Stallforth P
Chemistry?A European Journal , 24(17), 4202-4214 (2018)
L R Brunham et al.
The pharmacogenomics journal, 14(6), 555-563 (2014-05-28)
Differences in the frequency of pharmacogenomic variants may influence inter-population variability in drug efficacy and risk of adverse drug reactions (ADRs). We investigated the diversity of ∼ 4500 genetic variants in key drug-biotransformation and -response genes among three South East
Reaction of (S)-homoserine lactone with Grignard reagents: synthesis of amino-keto-alcohols and β-amino acid derivatives
Gundogdu O, et al.
Tetrahedron Asymmetry, 28(9), 1163-1168 (2017)
Walter Fast et al.
Trends in biochemical sciences, 37(1), 7-14 (2011-11-22)
N-Acyl-L-homoserine lactones (AHLs) are a major class of quorum-sensing signals used by Gram-negative bacteria to regulate gene expression in a population-dependent manner, thereby enabling group behavior. Enzymes capable of generating and catabolizing AHL signals are of significant interest for the
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