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Safety Information

900607

Sigma-Aldrich

2,5-Dibromohexanediamide

≥95%

Synonym(s):

2,5-Dibromoadipamide, DBHDA

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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:

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Certificates of Analysis (COA)

Lot/Batch Number
MKCP5689
MKCL4625
MKCC4980
MKCD5052

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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

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