Protection of asparagine and glutamine during N-alpha-Bpoc-based solid-phase peptide synthesis

被引：0

作者：

Carey, RI ^{[1
]}

Huang, HH ^{[1
]}

Wadsworth, JL ^{[1
]}

Burrell, CS ^{[1
]}

机构：

[1] UNIV GEORGIA,CTR METALLOENZYME STUDIES,ATHENS,GA 30602

来源：

INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH | 1996年 / 47卷 / 03期

关键词：

Bpoc; glutamine; asparagine; trityl; solid-phase peptide synthesis;

D O I：

暂无

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

In this paper we describe the synthesis and properties of Bpoc-Asn(Trt)-OH, Bpoc-Asn(Trt)-OPfp, Bpoc-Gln(Trt)-OH and Bpoc-Gln(Trt)-OPfp. These derivatives are highly soluble in CH2Cl2 and can be coupled efficiently in solid-phase peptide synthesis. The peptides, acetyl-Ala-Phe-Asn(Trt)-Gly-Leu-Ala-O-Dbf-SH and Boc-Cys(Acm)-Ala-Phe-Gln(Trt)-Gly-Leu-Ala-O-Dbf-SH (where O-Dbf-SH is the peptide ester of 4-mercapto-6-hydroxydibenzofuran) were synthesized by stepwise solid-phase peptide synthesis using N-alpha-Bpoc amino acids. We have observed that less than 0.1% of the trityl group is removed from the carboxamide of Gin and Asn during a standard 15 min N-alpha-Bpoc deprotection in 0.5% TFA in CH2Cl2. (C) Munksgaard 1996.

引用

页码：209 / 213

页数：5

共 21 条

[1] SYNTHESIS BY AN IMPROVED SOLID-PHASE METHOD OF A HIGHLY ACIDIC PEPTIDE FROM NUCLEOLAR NON-HISTONE PROTEIN-C23 [J].

COLOMBO, R .

BIOORGANIC CHEMISTRY, 1981, 10 (03) :219-232

[2]

FOTOUHI N, 1993, INT J PEPT PROT RES, V41, P153

[3] PEPTIDE-SYNTHESIS BY PRIOR THIOL CAPTURE .6. RATES OF THE DISULFIDE BOND FORMING CAPTURE REACTION AND DEMONSTRATION OF THE OVERALL STRATEGY BY SYNTHESIS OF THE C-TERMINAL 29-PEPTIDE SEQUENCE OF BPTI [J].

FOTOUHI, N ;

GALAKATOS, NG ;

KEMP, DS .

JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (12) :2803-2817

[4]

FOTOUHI N, 1972, INT J PEPT PROT RES, V40, P141

[5] PEPTIDES .36. SYNTHESIS OF THE 27-37 FRAGMENT OF A LYSOZYME ANALOG [J].

GALPIN, IJ ;

KENNER, GW ;

OHLSEN, SR ;

RAMAGE, R ;

SHEPPARD, RC ;

TYSON, RG .

TETRAHEDRON, 1979, 35 (23) :2785-2790

[6] USE OF AN ALLYLIC ANCHOR GROUP AND OF ITS PALLADIUM CATALYZED HYDROSTANNOLYTIC CLEAVAGE IN THE SOLID-PHASE SYNTHESIS OF PROTECTED PEPTIDE-FRAGMENTS [J].

GUIBE, F ;

DANGLES, O ;

BALAVOINE, G ;

LOFFET, A .

TETRAHEDRON LETTERS, 1989, 30 (20) :2641-2644

[7]

HAMMOND GS, 1958, J AM CHEM SOC, V80, P572

[8]

JUHASZ A, 1979, ACTA CHIM HUNG, V102, P289

[9] SYNTHESIS OF HUMAN INSULIN .3. PREPARATION OF A(14-21) - B(17-30) FRAGMENT [J].

KAMBER, B ;

RINIKER, B ;

SIEBER, P ;

RITTEL, W .

HELVETICA CHIMICA ACTA, 1976, 59 (08) :2830-2840

[10] SYNTHESIS OF A 39-PEPTIDE AND A 25-PEPTIDE BY THIOL CAPTURE LIGATIONS - OBSERVATION OF A 40-FOLD RATE ACCELERATION OF THE INTRAMOLECULAR O,N-ACYL-TRANSFER REACTION BETWEEN PEPTIDE-FRAGMENTS BEARING ONLY CYSTEINE PROTECTIVE GROUPS [J].

KEMP, DS ;

CAREY, RI .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (08) :2216-2222

← 1 2 3 →