Skip to Content
Merck
All Photos(2)

Documents

Safety Information

900607

Sigma-Aldrich

2,5-Dibromohexanediamide

≥95%

Synonym(s):

2,5-Dibromoadipamide, DBHDA

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

About This Item

Empirical Formula (Hill Notation):
C6H10Br2N2O2
CAS Number:
99584-96-0
Molecular Weight:
301.96
MDL number:
MFCD27976335
UNSPSC Code:
12352200
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

solid

storage temp.

2-8°C

InChI

1S/C6H10Br2N2O2/c7-3(5(9)11)1-2-4(8)6(10)12/h3-4H,1-2H2,(H2,9,11)(H2,10,12)

InChI key

PLSXNAQEJOGNKQ-UHFFFAOYSA-N

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

900607-BULK:
900607-VAR:
900607-250MG:

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’.

Already Own This Product?

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

Visit the Document Library

Posttranslational mutagenesis: A chemical strategy for exploring protein side-chain diversity.
Wright TH, et al.
Science, 4(354), 6312-6312 (2016)
Methods for converting cysteine to dehydroalanine on peptides and proteins.
Chalker JM, et al.
Chemical Science, 2, 1666-1676 (2011)
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)
Philip R Lindstedt et al.
Cell chemical biology, 28(1), 70-77 (2020-11-21)
Great advances have been made over the last four decades in therapeutic and diagnostic applications of antibodies. The activity maturation of antibody candidates, however, remains a significant challenge. To address this problem, we present a method that enables the systematic

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