TBDC TsOH, Advanced Carbodiimide Coupling Agents for Peptide Synthesis in Aqueous and Green Solvents. Carbodiimide for minimal protection LPPS.
CAS: 3082189-36-1
Synonym: N-tert-Butyl-N′-(3-dimethylaminopropyl)carbodiimide p-toluenesulfonic acid
N-tert-Butyl-N′-(3-dimethylammoniumpropyl)carbodiimide tosylate
Properties
Purity
≥98.0%
Molecular Formula
C17H29N3O3S
Molecular Weight
355,72 [gr/mol]
Appearance
White to off-white crystalline powder
Storage Conditions
Store in a cool place
Applications
TBDC (3-(((tert-butylimino)methylene)amino)-N,N-dimethylpropan-1-amine) salts represent a new generation of water- and organic-solvent-compatible coupling agents for peptide bond formation. These next-generation CDIs overcome key limitations of traditional reagents like EDC·HCl and DIC, offering:
- Minimal protection synthesis compatible. No need for protecting groups on His, Trp, Ser, Tyr, Thr
- High conversion (>95%) and low racemization (L:D > 95:5)
- Compatible with green solvents: EtOAc, 2-MeTHF, GVL, DMC
- Suitable for both manual and automated synthesis
- Forms open-chain stable intermediates unlike EDC
TBDC salts enable highly efficient amide bond formation in solution-phase, solid-phase, TAG – assisted LPPS ( TAPS) and green chemistry processes, eliminating the need for histidine and tryptophan side-chain protection in many cases.
Studies
Application No 320701 CARBODIIMIDES FOR USE AS A COUPLING AGENT
Publications
Enhancing Atom Economy via Minimal Protection-Liquid Phase Peptide Synthesis (MP-LPPS) Using TBDC Salts/Oxyma Pure
Dario Corbisiero, Nicola Patrian, Riccardo Grigolato, Alessandra Tiberti, Leonardo Rapisarda, Alessandra Tolomelli, Walter Cabri, and Lucia Ferrazzano
ACS Sustainable Chemistry & Engineering Article ASAP
Posters
- TBDCs: ADVANCED COUPLING REAGENTS FOR LIQUID PHASE PEPTIDE SYNTHESIS (LPPS) N. Patrian(1), D. Corbisiero(1), R. Grigolato(1), A. Tiberti(1), L. Rapisarda(1), L. Ferrazzano(1), A. Tolomelli(1), W. Cabri(1)(1) Department of Chemistry “G. Ciamician” Alma Mater Studiorum – University of Bologna, Via P. Gobbetti 85, 40126, Bologna View Poster
- TBDC® and QCD®: Novel water soluble carbodiimides for TAG assisted LPPS and minimal protection synthesis
Oleg Marder1, Srinivasa Rao Manne2, Hlobisile Nzama2, Beatriz G. de la Torre2, Fernando Albericio2, Alessandra Tolomelli3, Dario Corbisiero3, Lucia
Ferrazzano3, Nicola Patrian3 ,and Walter Cabri3View Poster - Strategic Optimization of Coupling Reactions and Green Solvents for Sustainable Peptide Manufacturing
MaheshKumar Cinthakunta Sridhar, Sayan Chakraborty & Nir Qvit
The Azrieli Faculty of Medicine in the Galilee, Bar Ilan University, Safed 1311502 , Israel View Poster