| 학회 | 한국공업화학회 |
| 학술대회 | 2015년 봄 (04/29 ~ 05/01, BEXCO (부산)) |
| 권호 | 19권 1호 |
| 발표분야 | 정밀화학_포스터 |
| 제목 | Efficient synthesis of natural aminopeptidase inhibitors, bestatin and AHPBA-Val |
| 초록 | Bestatin and AHPBA-Val are known as inhibitors to aminopeptidase N (APN). The bioactivity of bestatin and AHPBA-Val is closely related to the stereochemistry of β-amino-α-hydroxy acid moiety. However, the desired stereochemistry had been mostly given by chiral catalysts or chiral auxiliaries. Contrast to the previous reagent controlled methods, the chiral synthon for (2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid was stereoselectively prepared from the N-hydroxymethyl protected α-amino aldehyde via the intramolecular conjugate addition. The prepared synthon, trans-methoxymethyl-oxazolidine, was converted to bestatin and AHPBA-Val in 85% and 62% yields via 4 steps without separate production and deprotection steps of the vicinal amino alcohol. |
| 저자 | 서영란, 김영규, 채다원 |
| 소속 | 서울대 |
| 키워드 | Aminopeptidase inhibitors; bestatin; AHPBA-Val |
