Preparation of deuterated methyl and dimethyl substituted nicotinoylating agents for derivatization of the N-terminal of protein

被引：7

作者：

Tsumoto, H ^{[1
]}

Murata, C ^{[1
]}

Miyata, N ^{[1
]}

Taguchi, R ^{[1
]}

Kohda, K ^{[1
]}

机构：

[1] Nagoya City Univ, Grad Sch Pharmaceut Sci, Mizuho Ku, Nagoya, Aichi 4678603, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2003年 / 51卷 / 12期

关键词：

nicotinoylating agent; N-terminal; protein; mass spectrometry; D-label; differential expression analysis;

D O I：

10.1248/cpb.51.1399

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Methyl groups of 6-methylnicotinic acid and 2,6-dimethylnicotinic acid were deuterated by an H-D exchange reaction under conditions of 1% NaOD/D2O on heating. With a condensation reaction between the D-labeled nicotinic acid derivative and N-hydroxysuccinimide with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, the nicotinoylating agents, 1-(6-methyl-[D-3]nicotinoyloxy)succinimide (2c) and 1-(2,6-dimethy[D-6]nicotinoyloxy)succinimide (2f) were prepared. Both D-labeled nicotinoylating agents and their unlabeled counterparts quantitatively modified the N-terminal of protein.

引用

页码：1399 / 1401

页数：3

共 8 条

[1] A simple method for synthesis of active esters of isonicotinic and picolinic acids [J].

Christensen, JB .

MOLECULES, 2001, 6 (01) :47-51

[2]

Guo WJ, 1999, J NUCL MED, V40, P1563

[3] Quantitative analysis of complex protein mixtures using isotope-coded affinity tags [J].

Gygi, SP ;

Rist, B ;

Gerber, SA ;

Turecek, F ;

Gelb, MH ;

Aebersold, R .

NATURE BIOTECHNOLOGY, 1999, 17 (10) :994-999

[4]

KATO T, 1976, CHEM PHARM BULL, V24, P303

[5]

Miyagi M, 1998, RAPID COMMUN MASS SP, V12, P603, DOI 10.1002/(SICI)1097-0231(19980529)12:10<603::AID-RCM204>3.3.CO

[6]

2-S

[7] Quantitation and facilitated de novo sequencing of proteins by isotopic N-terminal labeling of peptides with a fragmentation directing moiety [J].

Munchbach, M ;

Quadroni, M ;

Miotto, G ;

James, P .

ANALYTICAL CHEMISTRY, 2000, 72 (17) :4047-4057

[8] EVALUATION OF THE BRAIN-SPECIFIC DELIVERY OF RADIOIODINATED (IODOPHENYL)ALKYL-SUBSTITUTED AMINES COUPLED TO A DIHYDROPYRIDINE CARRIER [J].

TEDJAMULIA, ML ;

SRIVASTAVA, PC ;

KNAPP, FF .

JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (11) :1574-1580

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