CHARACTERIZATION OF Z-BLOCKED ISOMERIC DIPEPTIDES BY FAST-ATOM-BOMBARDMENT TANDEM MASS-SPECTROMETRY AND KINETIC-ENERGY RELEASE MEASUREMENTS

被引：12

作者：

MAMMOLITI, E ^{[1
]}

SINDONA, G ^{[1
]}

UCCELLA, N ^{[1
]}

机构：

[1] UNIV CALABRIA,DIPARTIMENTO CHIM,I-87030 ARCAVACATA,ITALY

来源：

ORGANIC MASS SPECTROMETRY | 1992年 / 27卷 / 04期

关键词：

D O I：

10.1002/oms.1210270422

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Fast- and slow-reacting, protonated, Z-blocked (Z = benzyloxycarbonyl) phenylalanylphenylalanine and alanylphenylalanyl diasteromeric dipeptides undergo decarboxylation through two competing pathways assisted by the migration of the urethane benzyl group either to the terminal or to the amidic nitrogens. The reaction mechanism has been proved by tandem mass spectrometric experiments. The different kinetic energy released associated with CO2 elimination allows the distinction of the S,S from the R,S isomers by mass-analysed ion kinetic-energy experiments.

引用

页码：495 / 501

页数：7

共 19 条

[11]

JACKSON AE, 1976, SYNTHESIS-STUTTGART, P687

[12]

JONES JH, 1971, SPECIALISTIC PERIODI, V3, P238

[13] 2-(2-PYRIDYL-)ETHYL ESTERS - A NEW CARBOXYL PROTECTING GROUP IN PEPTIDE-SYNTHESIS [J].

KESSLER, H ;

BECKER, G ;

KOGLER, H ;

WOLFF, M .

TETRAHEDRON LETTERS, 1984, 25 (36) :3971-3974

[14]

LANE CF, 1975, SYNTHESIS-STUTTGART, P135

[15] BIOORGANIC APPLICATIONS OF MASS-SPECTROMETRY .5. TRANSMETHYLATION REACTIONS OF L-CARNITINE IN ENERGIZED CONDENSED PHASE [J].

LIGUORI, A ;

SINDONA, G ;

UCCELLA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (24) :7488-7491

[16]

OMODEISALE A, 1984, J CHEM RES-S, P50

[17] BIOORGANIC APPLICATIONS OF MASS-SPECTROMETRY .3. FAST-ATOM-BOMBARDMENT-INDUCED ZWITTERIONIC OLIGONUCLEOTIDE QUASI-MOLECULAR IONS SEQUENCED BY MS/MS [J].

PANICO, M ;

SINDONA, G ;

UCCELLA, N .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (17) :5607-5610

[18] SEQUENCE-SPECIFIC FRAGMENTATION OF BENZYLOXYCARBONYL DIPEPTIDES BY RESONANCE-ENHANCED MULTIPHOTON IONIZATION [J].

SEGAR, KR ;

JOHNSTON, MV .

ORGANIC MASS SPECTROMETRY, 1989, 24 (03) :176-182

[19]

TABET JC, 1990, SPECTROSC INT J, V4, P81

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