کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1346851 1500336 2015 7 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis of enantiopure l-(5-phenylfuran-2-yl)alanines by a sequential multienzyme process
ترجمه فارسی عنوان
سنتز آلانین های ال- (5-فنیل فوران-2-ییل) آلاینده های انانتیوپور به روش چند مرحله ای
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی معدنی
چکیده انگلیسی

The enantioselective synthesis of unnatural amino acids is an attractive goal. Increasing attention has been given in recent years to the development of dynamic kinetic resolution processes, providing the desired enantiomer in almost quantitative yields and with high enantiopurity. Herein we describe an efficient sequential multi-enzyme process for the preparation of enantiopure 5-phenylfuran-2-ylalanines l-4a–d, starting from racemic 2-acetamido-3-(5-phenylfuran-2-yl)propanoic acids rac-1a–d. The first step, the CaL-B-mediated dynamic kinetic resolution of the racemic oxazolones provided the N- and C-protected l-amino acids l-2a–d (81–92% ee) with 100% theoretical yield. The protecting groups were removed in excellent yields by a second (mild non-stereoselective PLE mediated hydrolysis of the ester) and a third (Acylase I catalyzed stereoselective hydrolysis of the amide) enzymatic step, thus increasing the enantiomeric excess of the target compounds over 99%.

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l-2-Amino-3-(5-phenylfuran-2-yl)propanoic acidC13H13NO3[α]D25 = +28.2 (c 1.0, CH3COOH)ee >99% on Astec Chirobiotic-Tag HPLC columnSource of chirality: Enzymatic resolutionAbsolute configuration: (S)

l-2-Amino-3-[5-(4-bromophenyl)furan-2-yl]propanoic acidC13H12BrNO3[α]D25 = +10.8 (c 1.0, CH3COOH)ee >99% on Astec Chirobiotic-Tag HPLC columnSource of chirality: Enzymatic resolutionAbsolute configuration: (S)

l-2-Amino-3-[5-(4-chlorophenyl)furan-2-yl]propanoic acidC13H12ClNO3[α]D25 = +17.8 (c 1.0, CH3COOH)ee >99% on Astec Chirobiotic-Tag HPLC columnSource of chirality: Enzymatic resolutionAbsolute configuration: (S)

l-2-Amino-3-[5-(2-chlorophenyl)furan-2-yl]propanoic acidC13H12ClNO3[α]D25 = +16.7 (c 1.0, CH3COOH)ee >99% on Astec Chirobiotic-Tag HPLC columnSource of chirality: Enzymatic resolutionAbsolute configuration: (S)

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron: Asymmetry - Volume 26, Issues 18–19, 15 October 2015, Pages 1095–1101
نویسندگان
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