Tetrahydrofuran amino acids:: Secondary structure in tetrameric and octameric carbopeptoids derived from a D-allo 5-(aminomethyl)tetrahydrofuran-2-carboxylic acid

被引：60

作者：

Hungerford, NL ^{[1
]}

Claridge, TDW ^{[1
]}

Watterson, MP ^{[1
]}

Aplin, RT ^{[1
]}

Moreno, A ^{[1
]}

Fleet, GWJ ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford Ctr Mol Sci, Oxford OX1 3QY, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 21期

关键词：

D O I：

10.1039/b002996n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of a D-allo-5-(azidomethyl)tetrahydrofuran-2-carboxylate as an amino acid precursor (in which the carboxylic acid is cis to the azidomethyl substituent and trans to the diol moiety) is reported from D-ribose. The oligomerisation of this monomer to dimeric, tetrameric and octameric carbopeptoids is described. NMR studies into the solution structures of cyclohexylidene-protected oligomers and of a deprotected tetramer with eight free hydroxy groups are described.

引用

页码：3666 / 3679

页数：14

共 37 条

[1]

BICHARD C, UNPUB

[2] ACETONIDES OF ALPHA-HYDROXY-DELTA-ALTRONOLACTONES [J].

BICHARD, CJF ;

FAIRBANKS, AJ ;

FLEET, GWJ ;

RAMSDEN, NG ;

VOGT, K ;

DOHERTY, O ;

PEARCE, L ;

WATKIN, DJ .

TETRAHEDRON-ASYMMETRY, 1991, 2 (09) :901-912

[3] CONFORMATIONAL-ANALYSIS OF LINEAR PEPTIDES .5. SPECTROSCOPIC CHARACTERIZATION OF BETA-TURNS IN AIB-CONTAINING OLIGOPEPTIDES IN CHLOROFORM [J].

BONORA, GM ;

MAPELLI, C ;

TONIOLO, C ;

WILKENING, RR ;

STEVENS, ES .

INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 1984, 6 (04) :179-188

[4] Folded conformation in peptides containing furanoid sugar amino acids [J].

Chakraborty, TK ;

Jayaprakash, S ;

Diwan, PV ;

Nagaraj, R ;

Jampani, SRB ;

Kunwar, AC .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (49) :12962-12963

[5] THE RING CONTRACTION OF DELTA-LACTONES WITH LEAVING GROUP ALPHA-SUBSTITUENTS - A STRATEGY FOR THE SYNTHESIS OF 2,5-DISUBSTITUTED HIGHLY FUNCTIONALIZED HOMOCHIRAL TETRAHYDROFURANS [J].

CHOI, SMS ;

MYERSCOUGH, PM ;

FAIRBANKS, AJ ;

SKEAD, BM ;

BICHARD, CJF ;

MANTELL, SJ ;

SON, JC ;

FLEET, GWJ ;

SAUNDERS, J ;

BROWN, D .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (21) :1605-1607

[6] An octameric carbopeptoid; Secondary structure in octameric and tetrameric 5-aminomethyl-tetrahydrofuran-2-carboxylates [J].

Claridge, TDW ;

Long, DD ;

Hungerford, NL ;

Aplin, RT ;

Smith, MD ;

Marquess, DG ;

Fleet, GWJ .

TETRAHEDRON LETTERS, 1999, 40 (11) :2199-2202

[7] Crystal structure of a fully protected β-O-galactosylated tripeptide [J].

Crisma, M ;

Gobbo, M ;

Toniolo, C ;

Rocchi, R .

CARBOHYDRATE RESEARCH, 1999, 315 (3-4) :334-338

[8] STRUCTURAL CHARACTERIZATION OF THE BETA-BEND RIBBON SPIRAL - CRYSTALLOGRAPHIC ANALYSIS OF 2 LONG (L-PRO-AIB)N SEQUENTIAL PEPTIDES [J].

DIBLASIO, B ;

PAVONE, V ;

SAVIANO, M ;

LOMBARDI, A ;

NASTRI, F ;

PEDONE, C ;

BENEDETTI, E ;

CRISMA, M ;

ANZOLIN, M ;

TONIOLO, C .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) :6273-6278

[9] Synthesis of tetrahydropyrans from sugar lactones [J].

Estevez, JC ;

Fairbanks, AJ ;

Fleet, GWJ .

TETRAHEDRON, 1998, 54 (44) :13591-13620

[10] SYNTHESIS OF 5-EPIHYDANTOCIDIN FROM D-RIBOSE [J].

FAIRBANKS, AJ ;

FLEET, GWJ .

TETRAHEDRON, 1995, 51 (13) :3881-3894

← 1 2 3 4 →