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 50 条

[41] Synthesis of a new chiral peptide analogue of DNA using ornithine subunits and solid-phase peptide synthesis methodologies
Lioy, E
Kessler, H
LIEBIGS ANNALEN, 1996, (02): : 201 - 204
[42] Direct access to side chain N,N′-diaminoalkylated derivatives of basic amino acids suitable for solid-phase peptide synthesis
Jean-Philippe Pitteloud
Nina Bionda
Predrag Cudic
Amino Acids, 2013, 44 : 321 - 333
[43] A NEW APPROACH TO THE SOLID-PHASE PEPTIDE-SYNTHESIS OF PEPTIDE ALKYL-AMIDES AND ESTERS
NICOLAS, E
CLEMENTE, J
PERELLO, M
ALBERICIO, F
PEDROSO, E
GIRALT, E
TETRAHEDRON LETTERS, 1992, 33 (16) : 2183 - 2186
[44] Solid-phase synthesis, characterization, and antibacterial activities of metallocene-peptide bioconjugates
Chantson, Janine T.
Falzacappa, Maria Vittoria Verga
Crovella, Sergio
Metzler-Nolte, Nils
CHEMMEDCHEM, 2006, 1 (11) : 1268 - 1274
[45] Direct solid-phase peptide synthesis on chitosan microparticles for targeting tumor cells
Meerovich, Igor
Smith, D. David
Dash, Alekha K.
JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY, 2019, 54
[46] Rapid solid-phase peptide synthesis using thermal and controlled microwave irradiation
Bacsa, Bernadett
Desai, Bimbisar
Dibo, Gabor
Kappe, C. Oliver
JOURNAL OF PEPTIDE SCIENCE, 2006, 12 (10) : 633 - 638
[47] Biofunctionalization of Nano Channels by Direct In-Pore Solid-Phase Peptide Synthesis
Brodrecht, Martin
Breitzke, Hergen
Gutmann, Torsten
Buntkowsky, Gerd
CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (67) : 17814 - 17822
[48] Amino acid bromides: their utilization for difficult couplings in solid-phase peptide synthesis
Ni, MH
Esposito, E
Kaptein, B
Broxterman, QB
Dal Pozzo, A
TETRAHEDRON LETTERS, 2005, 46 (37) : 6369 - 6371
[49] TEMPORARY SERINE PROTECTION IN SOLID-PHASE SYNTHESIS OF LH-RH ANALOGS
ARZENO, HB
BINGENHEIMER, W
BLANCHETTE, R
MORGANS, DJ
ROBINSON, J
INTERNATIONAL JOURNAL OF PEPTIDE AND PROTEIN RESEARCH, 1993, 41 (04): : 342 - 346
[50] p-Methoxyphenol: A potent and effective scavenger for solid-phase peptide synthesis
Samaca, Jhoan
Velandia-Bautista, Erika
Tabares, Luisa
Escamilla, Luis
Vanegas, Magnolia
Patarroyo, Manuel-E.
JOURNAL OF PEPTIDE SCIENCE, 2020, 26 (06)

← 1 2 3 4 5 →