Solution- and solid-phase synthesis of components for tethered bilayer membranes

被引：17

作者：

Bendavid, A

Burns, CJ

Field, LD

Hashimoto, K

Ridley, DD

Sandanayake, KRAS

Wieczorek, L

机构：

[1] Cooperat Res Ctr Mol Engn & Technol, Chatswood, NSW 2067, Australia

[2] CSIRO, Div Ind Phys, Lindfield, NSW 2070, Australia

[3] Univ Sydney, Sch Chem, Sydney, NSW 2006, Australia

[4] Ambri Pty Ltd, Chatswood, NSW 2067, Australia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 11期

关键词：

D O I：

10.1021/jo0057147

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of the novel compound PhCH2SS(C24H44N4O10)(C20H41) (5) for the preparation of tethered bilayer membranes is described. The compound is the all-amide analogue of the previously reported ester-containing membrane-forming material PhCH2SS( C24H40O14)(C20H41) (1) The advanced intermediate (C20H41) C16H28N3O8 (17) was prepared from the same starting materials using both solution-phase (13% yield) and solid-phase (81% yield) techniques. Monolayers on gold derived from 5 have been analyzed by ellipsometry and FTIR. The monolayers exhibit thicknesses similar to monolayers derived from 1 and possess H-bonded amide functionality.

引用

收藏

页码：3709 / 3716

页数：8

相关论文

共 54 条

[1] A MODIFIED POLYMER SUPPORT FOR ORGANIC-SYNTHESIS [J].

APSIMON, JW ;

DIXIT, DM .

SYNTHETIC COMMUNICATIONS, 1982, 12 (02) :113-116

[2]

BELLAMY LJ, 1959, INFRA RED SPECTRA CO

[3] Morphology and optical properties of gold thin films prepared by filtered are deposition [J].

Bendavid, A ;

Martin, PJ ;

Wieczorek, L .

THIN SOLID FILMS, 1999, 354 (1-2) :169-175

[4] FABRICATION OF SURFACES RESISTANT TO PROTEIN ADSORPTION AND APPLICATION TO 2-DIMENSIONAL PROTEIN PATTERNING [J].

BHATIA, SK ;

TEIXEIRA, JL ;

ANDERSON, M ;

SHRIVERLAKE, LC ;

CALVERT, JM ;

GEORGER, JH ;

HICKMAN, JJ ;

DULCEY, CS ;

SCHOEN, PE ;

LIGLER, FS .

ANALYTICAL BIOCHEMISTRY, 1993, 208 (01) :197-205

[5] INTERCHANGE BETWEEN MONOLAYERS ON GOLD FORMED FROM UNSYMMETRICAL DISULFIDES AND SOLUTIONS OF THIOLS - EVIDENCE FOR SULFUR SULFUR BOND-CLEAVAGE BY GOLD METAL [J].

BIEBUYCK, HA ;

WHITESIDES, GM .

LANGMUIR, 1993, 9 (07) :1766-1770

[6] The design and synthesis of simple molecular tethers for binding biomembranes to a gold surface [J].

Boden, N ;

Bushby, RJ ;

Clarkson, S ;

Evans, SD ;

Knowles, PF ;

Marsh, A .

TETRAHEDRON, 1997, 53 (31) :10939-10952

[7] Thiopeptide-supported lipid layers on solid substrates [J].

Bunjes, N ;

Schmidt, EK ;

Jonczyk, A ;

Rippmann, F ;

Beyer, D ;

Ringsdorf, H ;

Graber, P ;

Knoll, W ;

Naumann, R .

LANGMUIR, 1997, 13 (23) :6188-6194

[8] Synthesis of stereoisomerically pure monoether lipids [J].

Burns, CJ ;

Field, LD ;

Hashimoto, K ;

Petteys, BJ ;

Ridley, DD ;

Rose, M .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1999, 52 (05) :387-394

[9]

Burns CJ, 1999, AUST J CHEM, V52, P1071

[10] The AMBRI Biosensor - Stabilising artificial membranes and receptor attachment [J].

Burns, CJ ;

Braach-Maksvytis, VBL ;

King, LG ;

Osman, PDJ ;

Pace, RJ ;

Raguse, B ;

Wieczorek, L ;

Cornell, BA .

ADVANCED MATERIALS AND OPTICAL SYSTEMS FOR CHEMICAL AND BIOLOGICAL DETECTION, 1999, 3858 :17-24

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