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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:
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 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

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)
Koch, T. Buchardt, O.
Synthesis, 1065-1065 (1993)
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)
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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