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
Beilstein:
3912375
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
SMILES string
Br[H].N[C@H]1CCOC1=O
InChI
1S/C4H7NO2.BrH/c5-3-1-2-7-4(3)6;/h3H,1-2,5H2;1H/t3-;/m0./s1
InChI key
MKLNTBLOABOJFZ-DFWYDOINSA-N
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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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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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
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)
A new class of homoserine lactone quorum-sensing signals.
Schaefer AL, et al.
Nature, 454(7204), 595-599 (2008)
Koch, T. Buchardt, O.
Synthesis, 1065-1065 (1993)
Novel dual inhibitors of calpain and lipid peroxidation.
Auvin S, et al.
Bioorganic & Medicinal Chemistry Letters, 14(14), 3825-3828 (2004)
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