Skip to Content
MilliporeSigma
All Photos(2)

Key Documents

View All Documentation

471429

Sigma-Aldrich

(S)-(−)-α-Amino-γ-butyrolactone hydrobromide

99%

Synonym(s):

L-Homoserine lactone hydrobromide

Sign Into View Organizational & Contract Pricing
All Photos(2)

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

Quality Level

100

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

Looking for similar products? Visit Product Comparison Guide

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)

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000223217
0000226896
0000218261
MKCG2673
MKBK6941V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service