22849-49-6Relevant articles and documents
2,2'-Spirobi(1,3,2-benzodioxaphosphole): an Inexpensive and Effective Reagent for Peptide Synthesis
Cadogan, J. I. G.,Gosney, Ian,Randles, David,Yaslak, Salih,Ambler, Richard P.
, p. 298 - 299 (1982)
The readily accessible spirocyclic oxyphosphorane, 2,2'-spirobi(1,3,2-benzodioxaphosphole) (1), is a convenient and effective reagent for peptide coupling, racemisation as measured by the Izumiya test being strikingly suppressed 0.1percent in the presence of N-hydroxysuccinimide.
Effect of solvent on racemization in carbodiimide mediated solid phase fragment condensations
Haver,Smith
, p. 2239 - 2242 (1993)
The Izumiya tripeptide was used to assess racemization in solid-phase fragment condensations. Boc-Gly-Ala-OH1 was coupled to Leu-PAM resin with DIC in a variety of solvents, both with and without HOBt. After cleavage from the resin, the extent of racemization was determined using C18 RP-HPLC to separate the epimers. Solvents used were DMF, NMP, TFE, and each of these as mixtures with DCM. Also tested was a mixture of NMP and DMSO (85:15). Couplings in FMD/DCM (1:1) and NMP/DCM (1:1) in the presence of HOBt were in excess of 98% and racemization was undetectable (0.1%).
Amino Acids and Peptides. XXX. Phosphorus in Organic Synthesis. XVII. Application of Diphenyl Phosphorazidate (DPPA) and Diethyl Phosphorocyanidate (DEPC) to Solid-phase Peptide Synthesis
Ikota, Nobuo,Shioiri, Takayuki,Yamada, Shun-Ichi
, p. 3064 - 3069 (2007/10/02)
Two coupling reagents for peptide synthesis, diphenyl phosphorazidate (DPPA) and diethyl phosphorocyanidate (DEPC), were tested using the solid-phase method.The reactivities of DPPA and DEPC were examined by coupling Boc-Ile with Gly-resin.In a comparison