| 학회 | 한국공업화학회 |
| 학술대회 | 2015년 봄 (04/29 ~ 05/01, BEXCO (부산)) |
| 권호 | 19권 1호 |
| 발표분야 | 정밀화학_포스터 |
| 제목 | Efficient derivatization of a well-known aminopeptidase inhibitor bestatin |
| 초록 | Bestatin, (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl-L-leucine, not only shows effects on immunomodulation as an aminopeptidase inhibitor but is also used in the treatment of acute myelocytic leukemia. Several stereoselective total syntheses of bestatin and its derivatives such as 2-thiolbestatin or bestatin thioamide have been reported. In order to synthesize new kinds of bestatin analogs, we tried to substitute benzyl group on C-terminus with alkyl groups. The precursors for corresponding β-amino-α-hydroxy acids were prepared via intramolecular conjugate addition between PhSO2CH2NO2 and N-hydroxymethyl protected α-amino aldehydes. Therefore, the new isobutyl and isopropyl analogs of bestatin were produced in overall 51% and 38% yields from the corresponding α-amino aldehydes in 6 steps. |
| 저자 | 이수범, 서영란, 김영규 |
| 소속 | 서울대 |
| 키워드 | amino acid; bestatin |
