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471429

Sigma-Aldrich

(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:
15295-77-9
Molecular Weight:
182.02
Beilstein/REAXYS Number:
3912375
MDL number:
MFCD00674493
UNSPSC Code:
12352005
PubChem Substance ID:
24870732
NACRES:
NA.22

assay

99%

form

solid

optical activity

[α]20/D −21°, c = 1 in H2O

mp

225 °C (dec.) (lit.)

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Novel dual inhibitors of calpain and lipid peroxidation.
Auvin S, et al.
Bioorganic & Medicinal Chemistry Letters, 14(14), 3825-3828 (2004)
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)
A new class of homoserine lactone quorum-sensing signals.
Schaefer AL, et al.
Nature, 454(7204), 595-599 (2008)
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

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