Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries

被引：23

作者：

Simpson, Mark G. ^{[1
]}

Pittelkow, Michael ^{[1
]}

Watson, Stephen P. ^{[2
]}

Sanders, Jeremy K. M. ^{[1
]}

机构：

[1] Univ Cambridge, Univ Chem Lab, Cambridge CB2 1EW, England

[2] GlaxoSmithKline Med Res Ctr, Stevenage SG1 2NY, Herts, England

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 05期

基金：

英国生物技术与生命科学研究理事会;

关键词：

MOLECULAR AMPLIFICATION; THERMODYNAMIC CONTROL; GUEST BINDING; N-ACYL; RECEPTOR; SELECTION; ACID; ANTIBODIES; TEMPLATES; SYSTEMS;

D O I：

10.1039/b917145b

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe an efficient and general strategy for the synthesis of dimethyl acetal functionalised steroidal hydrazides based on the cholic acid skeleton with the aim of using these compounds as building blocks for dynamic combinatorial chemistry. Deprotection of the acetal protected building blocks with TFA leads to formation of libraries containing macrocyclic N-acyl hydrazone oligomers. The isolation of several of these, and their characterisation using NMR is described. The effects on the equilibrium library distribution by varying the substituents at C-7 and C-12, extending the side-chain with glycine, and inverting the configuration at C-3 are discussed. Finally, we report the exchange properties of these macrocycles and demonstrate new examples of proof-reading and self-sorting in dynamic combinatorial libraries.

引用

页码：1173 / 1180

页数：8

共 50 条

[11] Dissipative Dynamic Libraries (DDLs) and Dissipative Dynamic Combinatorial Chemistry (DDCC)
Del Giudice, Daniele
Spatola, Emanuele
Valentini, Matteo
Ercolani, Gianfranco
Di Stefano, Stefano
CHEMSYSTEMSCHEM, 2022, 4 (06)
[12] Symmetric building blocks and combinatorial functional group transformation as versatile strategies in combinatorial chemistry
Früchtel, JS
Pflugseder, K
Gstach, H
BIOTECHNOLOGY AND BIOENGINEERING, 2000, 71 (02) : 94 - 103
[13] Synthesis of cyclic oligomers from histidine-derived building blocks using dynamic combinatorial chemistry
Matsumoto, Masaomi
Nicholas, Kenneth M.
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24): : 9308 - 9313
[14] Synthesis of aromatic glycoconjugates. Building blocks for the construction of combinatorial glycopeptide libraries
Noerrlinger, Markus
Ziegler, Thomas
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2014, 10 : 2453 - 2460
[15] Combinatorial libraries from building blocks: Solid phase synthesis of semicarbazides.
Hoang, K
Baindur, N
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 217 : U1224 - U1224
[16] Dynamic combinatorial chemistry: Evolutionary formation and screening of molecular libraries
Eliseev, AV
Lehn, JM
COMBINATORIAL CHEMISTRY IN BIOLOGY, 1999, 243 : 159 - 172
[17] Systems chemistry: Pattern formation in random dynamic combinatorial libraries
Corbett, Peter T.
Sanders, Jeremy K. M.
Otto, Sijbren
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (46) : 8858 - 8861
[18] Peptide-based dynamic combinatorial libraries
Liu, Jingyuan
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U576 - U576
[19] ORGN 419-Expanding the scope of dynamic combinatorial chemistry: New building blocks for the development of novel receptors
Ingerman, Lindsey A.
Waters, Marcey L.
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2008, 235
[20] Dynamic Combinatorial Chemistry with Novel Dithiol Building Blocks: Towards New Structurally Diverse and Adaptive Screening Collections
Postma, Tobias M.
Galloway, Warren R. J. D.
Cougnon, Fabien B. L.
Pantos, G. Dan
Stokes, Jamie E.
Spring, David R.
SYNLETT, 2013, 24 (06) : 765 - 769

← 1 2 3 4 5 →