| 학회 | 한국공업화학회 |
| 학술대회 | 2016년 봄 (05/02 ~ 05/04, 여수 엑스포 컨벤션) |
| 권호 | 20권 1호 |
| 발표분야 | (정밀화학)신약후보물질과 바이오센서 개발 |
| 제목 | Divergent syntheses for aminopeptidase inhibitors |
| 초록 | threo-β-Amino-α-hydroxy acids are frequently found in natural aminopeptidase inhibitors, and they bind to the metals on metalloaminopeptidase. Since the structure of bestatin, one of the well-known natural metalloaminopeptidase inhibitors, was elucidated as [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine in 1976, various stereoselective methods are applied to synthesize optically pure bestatin. In this presentation, an efficient synthetic method for methyl trans-oxazolidine-5-carboxylate and its application to synthesize aminopeptidase inhibitors will be introduced. The stereoselective synthesis is started from a configurationally stable N-Boc-N-hydroxymethyl α-amino aldehyde, and the stereoselective intramolecular conjugation of N-hydroxymethyl group is utilized to achieve higher stereoselectivity. With the chiral synthons, bestatin and its new analogs are synthesized efficiently without the protection/deprotection steps of the corresponding vicinal amino alcohol moiety. |
| 저자 | 김영규, 서영란, 김봉현, 이수범 |
| 소속 | 서울대 |
| 키워드 | threo-β-Amino-α-hydroxy acids; stereoselective intramolecular conjugate addition |
