Backbone Amide Linker in Solid-Phase Synthesis

被引：84

作者：

Boas, Ulrik ^{[3
]}

Brask, Jesper ^{[2
]}

Jensen, Knud J. ^{[1
]}

机构：

[1] Univ Copenhagen, Dept Nat Sci, Fac Life Sci, DK-1871 Frederiksberg C, Denmark

[2] Novozymes AS, DK-2880 Bagsvaerd, Denmark

[3] Tech Univ Denmark, Natl Vet Inst, DK-1790 Copenhagen, Denmark

来源：

CHEMICAL REVIEWS | 2009年 / 109卷 / 05期

关键词：

TERMINAL PEPTIDE AMIDES; NATIVE CHEMICAL LIGATION; EXPLORING PRIVILEGED STRUCTURES; ON-RESIN CYCLIZATION; ACID PAL HANDLE; COMBINATORIAL SYNTHESIS; TRACELESS SYNTHESIS; SUPPORTED SYNTHESIS; BIOLOGICAL EVALUATION; REDUCTIVE AMINATION;

D O I：

10.1021/cr068206r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A comprehensive survey of the Backbone Amide Linker (BAL) chemical methodology, which extends beyond applications in peptide chemistry, is provided. The theories used in the implementation of BAL chemistry include attaching the aromatic aldehyde to the support and perform the reductive amination (RA) on-resin. A direct strategy for measuring of reactions on the trialkoxybenzyl BAL handle is provided by introduction of a 13C label at the aldehyde moiety used to monitor reactions leading to BAL-carbamate formation. The OHBAL linker is attached to the solid phase via a Sieber linker, allowing the release of the entire substrate-BAL adduct by treatment with trifluoroacetic acid-DCM (TFA-DCM). A way to extend the peptide C-terminally from the BAL-anchored residue is described to access peptides with C-termini labile to nucleophiles.

引用

页码：2092 / 2118

页数：27

共 190 条

[31] On-bead chemical synthesis and display of phosphopeptides for affinity pull-down proteomics [J].

Brandt, M ;

Madsen, JC ;

Bunkenborg, J ;

Jensen, ON ;

Gammeltoft, S ;

Jensen, KJ .

CHEMBIOCHEM, 2006, 7 (04) :623-630

[32] Microwave heating for solid-phase peptide synthesis: General evaluation and application to 15-mer phosphopeptides [J].

Brandt, Malene ;

Gammeltoft, Steen ;

Jensen, Knud J. .

INTERNATIONAL JOURNAL OF PEPTIDE RESEARCH AND THERAPEUTICS, 2006, 12 (04) :349-357

[33] Fmoc solid-phase synthesis of peptide thioesters by masking as trithioortho esters [J].

Brask, J ;

Albericio, F ;

Jensen, KJ .

ORGANIC LETTERS, 2003, 5 (16) :2951-2953

[34] Monolayer assemblies of a de novo designed 4-α-helix bundle carboprotein and its sulfur anchor fragment on Au(111) surfaces addressed by voltammetry and in situ scanning tunneling microscopy [J].

Brask, J ;

Wackerbarth, H ;

Jensen, KJ ;

Zhang, JD ;

Chorkendorff, I ;

Ulstrup, J .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (01) :94-104

[35] Monosaccharide templates for de novo designed 4-α-helix bundle proteins:: template effects in carboproteins [J].

Brask, J ;

Dideriksen, JM ;

Nielsen, J ;

Jensen, KJ .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (13) :2247-2252

[36] Carboproteins:: A 4-α-helix bundle protein model assembled on a D-galactopyranoside template [J].

Brask, J ;

Jensen, KJ .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (05) :697-700

[37]

Brask J, 2000, J PEPT SCI, V6, P290, DOI 10.1002/1099-1387(200006)6:6<290::AID-PSC257>3.0.CO

[38]

2-L

[39]

Brink H.T. T., 2006, J OFPEPTIDE SCI, V12, P686

[40] Merrifield, alpha-methoxyphenyl (MAMP) resin; A new versatile solid support for the synthesis of secondary amides. [J].

Brown, DS ;

Revill, JM ;

Shute, RE .

TETRAHEDRON LETTERS, 1998, 39 (46) :8533-8536

← 1 2 3 4 5 6 7 8 9 10 →