Application of microwave irradiation to the synthesis of 14-helical β-peptides

被引：88

作者：

Murray, JK ^{[1
]}

Gellman, SH ^{[1
]}

机构：

[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA

来源：

ORGANIC LETTERS | 2005年 / 7卷 / 08期

关键词：

D O I：

10.1021/ol0501727

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] We have evaluated the effects of microwave irradiation on the solid-phase synthesis of beta-peptides. Sequences designed to adopt the 14-helix, especially those containing the structure-promoting residue trans-2-aminocyclohexanecarboxylic acid (ACHC), suffer from poor synthetic efficiency under standard SPPS conditions. A comparison of microwave and conventional heating shows that both provide excellent synthetic results for shorter sequences; however, we identify a clear benefit from microwave irradiation for longer beta-peptides.

引用

页码：1517 / 1520

页数：4

共 32 条

[1] Developments in peptide and amide synthesis
Albericio, F
[J]. CURRENT OPINION IN CHEMICAL BIOLOGY, 2004, 8 (03) : 211 - 221
[2] Synthesis and characterization of trans-2-aminocyclohexanecarboxylic acid oligomers:: An unnatural helical secondary structure and implications for β-peptide tertiary structure
Appella, DH
Christianson, LA
Karle, IL
Powell, DR
Gellman, SH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (26) : 6206 - 6212
[3] Formation of short, stable helices in aqueous solution by β-amino acid hexamers
Appella, DH
Barchi, JJ
Durell, SR
Gellman, SH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (10) : 2309 - 2310
[4] beta-peptide foldamers: Robust Helix formation in a new family of beta-amino acid oligomers
Appella, DH
Christianson, LA
Karle, IL
Powell, DR
Gellman, SH
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) : 13071 - 13072
[5] Syntheses and CD-spectroscopic investigations of longer-chain β-peptides:: Preparation by solid-phase couplings of single amino acids, dipeptides, and tripeptides
Arvidsson, PI
Frackenpohl, J
Seebach, D
[J]. HELVETICA CHIMICA ACTA, 2003, 86 (05) : 1522 - 1553
[6] Design, machine synthesis, and NMR-solution structure of a β-heptapeptide forming a salt-bridge stabilised 314-helix in methanol and in water
Arvidsson, PI
Rueping, M
Seebach, D
[J]. CHEMICAL COMMUNICATIONS, 2001, (07) : 649 - 650
[7] A one-bead, one-stock solution approach to chemical genetics:: part 1
Blackwell, HE
Pérez, L
Stavenger, RA
Tallarico, JA
Eatough, EC
Foley, MA
Schreiber, SL
[J]. CHEMISTRY & BIOLOGY, 2001, 8 (12): : 1167 - 1182
[8] AN EFFICIENT METHOD FOR ANCHORING FMOC-AMINO ACIDS TO HYDROXYL-FUNCTIONALIZED SOLID SUPPORTS
BLANKEMEYERMENGE, B
NIMTZ, M
FRANK, R
[J]. TETRAHEDRON LETTERS, 1990, 31 (12) : 1701 - 1704
[9] Erdélyi M, 2002, SYNTHESIS-STUTTGART, P1592
[10] Focused™ microwave instrumentation from CEM corporation
Ferguson, J. Doug
[J]. MOLECULAR DIVERSITY, 2003, 7 (2-4) : 281 - 286

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