471429
(S)-(−)-α-Amino-γ-butyrolactone hydrobromide
99%
Synonym(s):
L-Homoserine lactone hydrobromide
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About This Item
Empirical Formula (Hill Notation):
C4H7NO2 · HBr
CAS Number:
Molecular Weight:
182.02
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3912375
Assay:
99%
Form:
solid
Product Name
(S)-(−)-α-Amino-γ-butyrolactone hydrobromide, 99%
InChI
1S/C4H7NO2.BrH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1
SMILES string
Br[H].N[C@H]1CCOC1=O
InChI key
MKLNTBLOABOJFZ-DFWYDOINSA-N
assay
99%
form
solid
optical activity
[α]20/D −21°, c = 1 in H2O
mp
225 °C (dec.) (lit.)
functional group
ester
storage temp.
2-8°C
Quality Level
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Application
(S)-(-)-α-Amino-γ-butyrolactone hydrobromide may be used as a building block to prepare:
- β-ketoamide N-acylated-L-homoserine lactones (AHLs) as quorum sensing molecules
- p-coumaroyl-HSL (homoserine lactone)
- calpain and lipid peroxidation inhibitors
Used to prepare pseudopeptide inhibitors for Ras farnesyl-protein transferase as well as selenomethionine.
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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S L Graham et al.
Journal of medicinal chemistry, 37(6), 725-732 (1994-03-18)
Inhibitors of Ras farnesyl-protein transferase are described. These are reduced pseudopeptides related to the C-terminal tetrapeptide of the Ras protein that signals farnesylation. Deletion of the carbonyl groups between the first two residues of the tetrapeptides either preserves or improves
Novel dual inhibitors of calpain and lipid peroxidation.
Auvin S, et al.
Bioorganic & Medicinal Chemistry Letters, 14(14), 3825-3828 (2004)
A new class of homoserine lactone quorum-sensing signals.
Schaefer AL, et al.
Nature, 454(7204), 595-599 (2008)
Robust routes for the synthesis of N-acylated-L-homoserine lactone (AHL) quorum sensing molecules with high levels of enantiomeric purity.
Hodgkinson JT, et al.
Tetrahedron Letters, 52(26), 3291-3294 (2011)
Koch, T. Buchardt, O.
Synthesis, 1065-1065 (1993)
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