900607

Sigma-Aldrich

2,5-Dibromohexanediamide

≥95%

Synonym(s):
2,5-Dibromoadipamide, DBHDA
Empirical Formula (Hill Notation):
C6H10Br2N2O2
CAS Number:
Molecular Weight:
301.96
MDL number:
NACRES:
NA.22

Quality Level

assay

≥95%

form

solid

storage temp.

2-8°C

Application

This compound has been shown to be a useful reagent for the conversion of cysteine to dehydroalanine (DHA) in peptides or proteins. This enables chemical mutagenesis in which DHA can be efficiently reacted with iodide building blocks to add various natural and unnatural side chains on proteins. It was also shown that other modifications could be added through DHA such as phosphorylation, methylation, and glycosylation. In other research it was shown that DHA can be used to make ubiquitin conjugates that have a bond that mimics the native isopeptide bond.

Packaging

250 mg in glass insert

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
Methods for converting cysteine to dehydroalanine on peptides and proteins.
Chalker JM, et al.
Chemical Science, 2, 1666-1676 (2011)
Posttranslational mutagenesis: A chemical strategy for exploring protein side-chain diversity.
Wright TH, et al.
Science, 4(354), 6312-6312 (2016)
Protein ubiquitination via dehydroalanine: development and insights into the diastereoselective 1,4-addition step.
Meledin R, et al.
Organic & Biomolecular Chemistry, 14(21), 4817-4823 (2016)

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