72122-63-5Relevant articles and documents
HOAt.DCHA as co-coupling agent in the synthesis of peptides employing Fmoc-amino acid chlorides as coupling agents: Application to the synthesis of ss-casomorphin
Sureshbabu, Vommina V.,Chennakrishnareddy, Gundala
experimental part, p. 981 - 988 (2009/12/28)
A simple, efficient and racemization free method for the synthesis of peptides employing Fmoc-amino acid chlorides mediated by HOAtDCHA as a co-coupling agent has been described. This protocol is successfully employed in the synthesis of the pentapeptide H-Pro-Gly-VaI-GIy-VaI-OH (PGVGV), and ss-casomorphin (H-Tyr-Pro-Phe-Pro-Gly-OH) in 85 and 80% yields, respectively.
HOBt·DCHA-mediated synthesis of sterically hindered peptides employing Fmoc-amino acid chlorides in both solution-phase and solid phase methods
Sureshbabu, Vommina V.,Sudarshan, Naremaddepalli S.,Chenna Krishna
, p. 2625 - 2637 (2008/12/22)
The synthesis of peptides employing Fmoc-amino acid chlorides in presence of HOBt·DCHA salt in solution as well as by the solid-phase methods is described. The coupling was found to be complete in 30 min and free from racemization. The synthesis of β-casomorphin by solid-phase protocol employing Fmoc-amino acid chloride/HOBt·DCHA in DMF-CH2Cl2 has also been outlined. The final peptide was obtained in 80% yield and was fully characterized. Copyright Taylor & Francis Group, LLC.
A rapid and efficient synthesis of β-casomorphin employing Boc-amino acids and 9-fluorenylmethyl chloroformate as a coupling agent
Babu, V.V. Suresh,Tantry
, p. 2708 - 2712 (2007/10/03)
The synthesis of β-casomorphin H-Tyr-Pro-Phe-Pro-Gly-OH employing Boc group for Nα-protection and 9-fluorenylmethyl chloroformate (Fmoc-Cl) for the formation of peptide bond is described. The protocol employing Fmoc-Cl as coupling reagent is found to be simple, efficient and rapid. All the intermediate peptides as well as the final protected peptide Boc-Tyr( iBu)-Pro-Phe-Pro-Gly-OMe have been isolated and fully characterized. They have been obtained in good yield and with high purity.
Synthesis of β-casomorphin employing Fmoc-amino acid chlorides and t-butyldimethylsilyloxy benzotriazole (TBDMS-OBt)
Tantry, Subramanyam J.,Mathad, Raveendra I.,Suresh Babu, Vommina V.
, p. 2104 - 2108 (2007/10/03)
Coupling of Fmoc-amino acid chlorides can be carried out using t-butyldimethylsilyloxy benzotriazole, the reaction being carried out in organic medium. No addition of base is required. The coupling is fast and racemization free. The workup and isolation of product are easy. Thus, the synthesis of β-casomorphin (Tyr-Pro-Phe-Pro-Gly) is accomplished.
Coupling in the absence of a tertiary base: A method for the deprotonation of hydrochloride salts of peptide esters to free amino peptide esters
Tantry, Subramanyam J.,Ananda,Suresh Babu
, p. 1028 - 1031 (2007/10/03)
The deprotonation of hydrochloride salts of peptide esters is accomplished using activated zinc dust. The reaction is neat and quantitative. Addition of a tertiary base is eliminated during the coupling. The free amino peptide esters have been isolated in good yield and purity. This method is extended for the synthesis of β-casomorphin (Tyr-Pro-Phe-Pro-Gly). During its synthesis, all the intermediate free amino peptide esters have been isolated and characterized.
Fmoc-peptide acid chlorides in fragment coupling: Synthesis of β- casomorphin by 3+2 divergent approach
Suresh Babu,Gayathri,Gopi
, p. 79 - 91 (2007/10/03)
Fmoc-peptide acid chlorides are prepared and used as rapid and efficient coupling agents in fragment coupling. Thus the synthesis of the model tetrapeptide Leu-Ala-Gly-Val and β-casomorhin (Tyr-Pro-Phe-Pro-Gly) are accomplished by the (2+2) and (3+2) divergent approach respectively.
Synthesis of peptides mediated by AgCN
Suresh Babu,Gayathri
, p. 1109 - 1113 (2007/10/03)
The acylation reactions employing Fmoc-amino acid chlorides have been carried out in the presence of AgCN. There is no addition of any base. The coupling is fast and racemization free. The work up and the isolation of products are easy. Thus the synthesis of several dipeptides, a model tetrapeptide, Leu-Ala-Gly-Val and β-casomorphin (Tyr-Pro-Phe-Pro-Gly) are accomplished.
Fmoc-amino acid chlorides-KOBt in solid phase peptide synthesis
Sivanandaiah, K. M.,Babu, V. V. Suresh,Gangadhar, B. P.
, p. 620 - 623 (2007/10/02)
Fmoc-amino acid chlorides can be used along with KOBt instead of the routinely employed 1:1 mixture of base (TEA or DIEA) and catalyst (HOBt or Piv) in solid phase peptide synthesis.No additional base is required.Coupling is fast and racemization free.Thus, the opioid peptide, β-casomorphin (Tyr-Pro-Phe-Pro-Gly) and the laminin fragment, Tyr-Ile-Gly-Ser-Arg-NH2 have been obtained in good yields as well as purity.
SYNTHESIS AND FAST-ATOM BOMBARDMENT MASS SPECTROMETRY OF β-CASOMORPHIN-5
Banfi, Stefano,Rubino, Federico Maria,Sommaruga, Maurizio,Restani, Patrizia
, p. 41 - 46 (2007/10/02)
A fully detailed solution synthesis of β-casomorphin-5 (Tyr-Pro-Phe-Pro-Gly) and positive FAB mass spectra of all synthetic intermediates are reported, together with the B/E daughter ion spectrum of the peptide, and the corresponding sequence determination.
