5-TAMRA Cadaverine

Product Introduction

5-TAMRA cadaverine can used to modify carboxylic acid group in the presence of activators (e.g. EDC, or DCC) or activated esters (e.g. NHS esters) through a stable amide bond. It also can be reversibly coupled to aldehydes and ketones to form a Schiff base-which can be reduced to a generate stable amine derivative by sodium borohydride (NaBH4) or sodium cyanoborohydride (NaCNH3).
Although the mixed isomers of 5(6)-TAMRA cadaverine is a preferred, routinely used orange-fluorescent dye for staining proteins, it is rearly used for labeling peptides and nucleotides. Purification of 5(6)-TAMRA labeled peptide and nucleotides might be troublesome due to significant signal broadening in HPLC purification. Peptides and nucleotides labeled with a single isomer TAMRA usually give better resolution in HPLC purification that is often required in the conjugation processes.

Chemical Information
Synonyms	5-TAMRA cadaverine TFA salt; Tetramethylrhodamine 5-carboxamide cadaverine
IUPAC Name	5-(5-aminopentylcarbamoyl)-2-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]benzoate
Canonical SMILES	CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=C(C=C(C=C4)C(=O)NCCCCCN)C(=O)[O-]
InChI	InChI=1S/C30H34N4O4/c1-33(2)20-9-12-23-26(17-20)38-27-18-21(34(3)4)10-13-24(27)28(23)22-11-8-19(16-25(22)30(36)37)29(35)32-15-7-5-6-14-31/h8-13,16-18H,5-7,14-15,31H2,1-4H3,(H-,32,35,36,37)
InChI Key	GGMFTOCYWNYUSU-UHFFFAOYSA-N
Solubility	DMSO, DMF, MeOH

Computed Properties
XLogP3	0.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	8
Exact Mass	514.25800558 g/mol
Monoisotopic Mass	514.25800558 g/mol
Topological Polar Surface Area	111Ų
Heavy Atom Count	38
Formal Charge	0
Complexity	974
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Patents

Publication Number	Title	Priority Date
US-10195289-B2	Engineered polypeptide conjugates using transglutaminase	2013-07-31
US-10842881-B2	Engineered polypeptide conjugates using transglutaminase	2013-07-31
US-2021162058-A1	Engineered polypeptide conjugates using transglutaminase	2013-07-31
US-9676871-B2	Engineered polypeptide conjugates and methods for making thereof using transglutaminase	2010-11-05
US-10941216-B2	Engineered polypeptide conjugates and methods for making thereof using transglutaminase	2010-11-05