Penicillin acylase-mediated synthesis of 2-acetyl-1-pyrroline and of 2-propionyl-1-pyrroline, key roast-smelling odorants in food. Inclusion complexes with beta-cyclodextrin and their NMR and MS characterization

被引：35

作者：

Favino, TF ^{[1
]}

Fronza, G ^{[1
]}

Fuganti, C ^{[1
]}

Fuganti, D ^{[1
]}

Grasselli, P ^{[1
]}

Mele, A ^{[1
]}

机构：

[1] POLITECN MILAN,CTR CNR CHIM SOSTANZE ORGAN NAT,DIPARTIMENTO CHIM,I-20131 MILAN,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1996年 / 61卷 / 25期

关键词：

D O I：

10.1021/jo961474c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the strong natural roast odorants 1 and 2 is achieved from the C-6 isomeric alcohols 16 and 21 via the acetylenic C-6 and C-7 amines 8 and 9, Key step in the process is the hydrolysis of the N-phenylacetamides 12 and 13 by means of immobilized penicillin acylase, which affords the 1-amino-4,5-diketones 14 and 15, spontaneously ring closing to 1 and 2. These latter compounds form inclusion complexes with beta-cyclodextrin, as demonstrated by NMR measurements in deuterated water and FAB-MS spectra.

引用

页码：8975 / 8979

页数：5