Abstract
The Izumiya tripeptide was used to assess racemization in solid-phase fragment condensations. Boc-Gly-Ala-OH1 was coupled to Leu-PAM resin 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-HLPC 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 DMF/DCM (1:1) and NMP/DCM (1:1) in the presence of HOBt were in excess of 98% and racemization was undetectable. (<0.1%).
Original language | English (US) |
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Pages (from-to) | 2239-2242 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 34 |
Issue number | 14 |
DOIs | |
State | Published - Apr 2 1993 |
All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry