Synthesis of pyrraline reference material

被引：64

作者：

Henle, T

Bachmann, A

机构：

[1] Lehrstuhl für Milchwissenschaft, Technische Universität München, D-85350 Freising-Weihenstephan

来源：

ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG | 1996年 / 202卷 / 01期

关键词：

Maillard reaction; 2-amino-6-(2-formyl-5-hydroxymethyl-1-pyrrolyl)-hexanoic acid (registry no 74509-14-1); pyrraline;

D O I：

10.1007/BF01229689

中图分类号：

TS2 [食品工业];

学科分类号：

0832 ;

摘要：

A simplified and improved method is described for the preparation of pyrraline, a lysine derivative from the advanced Maillard reaction and potential indicator for heat treatment of foods. The compound was obtained in a high degree of purity and with a yield of 31% from N-alpha-t-butyloxycarbonyl-L-lysine after heating with 3-deoxy-D-erythro-hexos-2-ulose for 2h at 70 degrees C in the dry state, preparative fractionation of the resulting N-alpha-t-butyloxycarbonyl pyrraline with reverse-phase liquid chromatography and final deprotection of the intermediate compound with acetic acid.

引用

收藏

页码：72 / 74

页数：3

相关论文

共 15 条

[1] HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHIC DETERMINATION OF EPSILON-PYRROLE-LYSINE IN PROCESSED FOOD [J].

CHIANG, GH .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1988, 36 (03) :506-509

[2]

HAYASE F, 1989, J BIOL CHEM, V363, P3758

[3] DETERMINATION OF PROTEIN-BOUND 2-AMINO-6-(2-FORMYL-1-PYRROLYL)-HEXANOIC ACID (PYRRALINE) BY ION-EXCHANGE CHROMATOGRAPHY AND PHOTODIODE ARRAY DETECTION [J].

HENLE, T ;

KLOSTERMEYER, H .

ZEITSCHRIFT FUR LEBENSMITTEL-UNTERSUCHUNG UND-FORSCHUNG, 1993, 196 (01) :1-4

[4]

HENLE T, 1994, MAILLARD REACTIONS C, P195

[5] AN IMPROVED PREPARATION OF 3-DEOXY-D-ERYTHRO-HEXOS-2-ULOSE VIA THE BIS(BENZOYLHYDRAZONE) AND SOME RELATED CONSTITUTIONAL STUDIES [J].

MADSON, MA ;

FEATHER, MS .

CARBOHYDRATE RESEARCH, 1981, 94 (02) :183-191

[6] FORMATION OF AROMATIC-COMPOUNDS FROM CARBOHYDRATES .9. REACTION OF D-GLUCOSE AND L-LYSINE IN SLIGHTLY ACIDIC, AQUEOUS-SOLUTION [J].

MILLER, R ;

OLSSON, K ;

PERNEMALM, PA .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1984, 38 (08) :689-694

[7] SYNTHESIS OF (+/-)-2-FORMYL-5-(HYDROXYMETHYL)PYRROLE-1-NORLEUCINE - A BIOLOGICALLY-ACTIVE MAILLARD REACTION-PRODUCT DERIVED FROM GLUCOSE AND LYSINE [J].

MILLER, R ;

OLSSON, K .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1985, 39 (09) :717-723

[8] FORMATION OF EPSILON-(2-FORMYL-5-HYDROXYMETHYL-PYRROL-1-YL)-L-NORLEUCINE IN THE MAILLARD REACTION BETWEEN D-GLUCOSE AND L-LYSINE [J].

NAKAYAMA, T ;

HAYASE, F ;

KATO, H .

AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1980, 44 (05) :1201-1202

[9]

OMURA H, 1983, ACA S SER, V5, P537

[10]

OSTE RE, 1987, J AGR FOOD CHEM, V35, P938, DOI 10.1021/jf00078a020