Regiospecific alkylation of histidine and histamine at N-1 (tau)

被引：51

作者：

Jain, R ^{[1
]}

Cohen, LA ^{[1
]}

机构：

[1] NIDDK,BIOORGAN CHEM LAB,NIH,BETHESDA,MD 20892

来源：

TETRAHEDRON | 1996年 / 52卷 / 15期

关键词：

D O I：

10.1016/0040-4020(96)00187-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Series of 1-alkyl histidines and histamines have been synthesized by the alkylation of the corresponding 5,6,7,8-tertrahydro-5-oxoimidazo[1,5-c]pyrimidines with alkyl halides in aprotic solvents. The method of conversion of the intermediate quaternary salt to the aminoacid or amine depends oil the nature of the alkyl group.

引用

收藏

页码：5363 / 5370

页数：8

相关论文

共 21 条

[1]

[Anonymous], 1972, J BIOL CHEM, V247, P977

[2] SYNTHESIS OF N-EPSILON-(P-BROMOPHENYL)-L-LYSINE AND N-TAU-(P-BROMOPHENYL)-L-HISTIDINE AS MODELS FOR ADDUCTS OF BROMOBENZENE 3,4-OXIDE TO PROTEIN - OBSERVATION OF AN UNUSUAL PD-CATALYZED N-TAU-ARYL TO N-PI-ARYL SUBSTITUENT MIGRATION [J].

BAMBAL, R ;

HANZLIK, RP .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (04) :729-732

[3] SYNTHESIS OF N-PI-(2-HYDROXYETHYL)-L-HISTIDINES AND "N-TAU-(2-HYDROXYETHYL)-L-HISTIDINES [J].

CALLEMAN, CJ ;

WACHTMEISTER, CA .

ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1979, 33 (04) :277-280

[4] FETAL LAMB 3-BETA,20-ALPHA-HYDROXYSTEROID OXIDOREDUCTASE - DUAL ACTIVITY AT THE SAME ACTIVE-SITE EXAMINED BY AFFINITY LABELING WITH 16-ALPHA-(BROMO[2'-C-14]ACETOXY)PROGESTERONE [J].

CHEN, QX ;

ROSIK, LO ;

NANCARROW, CD ;

SWEET, F .

BIOCHEMISTRY, 1989, 28 (22) :8856-8863

[5] USE OF MIN-DINITROPHENYLHISTIDINE IN SOLID-PHASE SYNTHESIS OF TRICOSAPEPTIDES 124-146 OF HUMAN HEMOGLOBIN BETA CHAIN [J].

CHILLEMI, F ;

MERRIFIELD, RB .

BIOCHEMISTRY, 1969, 8 (11) :4344-+

[6] PHENACYL-DIRECTED ALKYLATION OF IMIDAZOLES - A NEW REGIOSPECIFIC SYNTHESIS OF 3-SUBSTITUTED L-HISTIDINES [J].

CHIVIKAS, CJ ;

HODGES, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) :3591-3594

[7] AMINO-ACIDS AND PEPTIDES .45. THE PROTECTION OF THE THIOL FUNCTION OF CYSTEINE AND THE IMIDAZOLE-N OF HISTIDINE BY THE DIPHENYL-4-PYRIDYLMETHYL GROUP [J].

COYLE, S ;

HALLETT, A ;

MUNNS, MS ;

YOUNG, GT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (02) :522-528

[8] BENZO[A]PYRENE ANTI-DIOL EPOXIDE COVALENTLY MODIFIES HUMAN SERUM-ALBUMIN CARBOXYLATE SIDE-CHAINS AND IMIDAZOLE SIDE-CHAIN OF HISTIDINE(146) [J].

DAY, BW ;

SKIPPER, PL ;

ZAIA, J ;

TANNENBAUM, SR .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (22) :8505-8509

[9] POTENTIAL HISTAMINE H2-RECEPTOR ANTAGONISTS .3. METHYLHISTAMINES [J].

DURANT, GJ ;

EMMETT, JC ;

GANELLIN, CR ;

ROE, AM ;

SLATER, RA .

JOURNAL OF MEDICINAL CHEMISTRY, 1976, 19 (07) :923-928

[10] STRUCTURAL ELUCIDATION AND PROPERTIES OF 8ALPHA-(N1-HISTIDYL)RIBOFLAVIN - FLAVIN COMPONENT OF THIAMINE DEHYDROGENASE AND BETA-CYCLOPIAZONATE OXIDOCYCLASE [J].

EDMONDSON, DE ;

KENNEY, WC ;

SINGER, TP .

BIOCHEMISTRY, 1976, 15 (14) :2937-2945