PATIC: a conformationally constrained photoisomerizable amino acid

被引：7

作者：

Zhang, J ^{[1
]}

James, DA ^{[1
]}

Woolley, GA ^{[1
]}

机构：

[1] Univ Toronto, Dept Chem, Toronto, ON M5S 3H6, Canada

来源：

JOURNAL OF PEPTIDE RESEARCH | 1999年 / 53卷 / 05期

关键词：

caged compound; light; peptide design; photochromic; photoisomer; photoregulated; S-peptide;

D O I：

10.1034/j.1399-3011.1999.00061.x

中图分类号：

Q5 [生物化学];

学科分类号：

071010 ; 081704 ;

摘要：

The synthesis of a conformationally constrained photoisomerizable amino acid, phenylazo-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid (PATIC), is described. This amino acid can be incorporated into peptides using standard Fmoc procedures and can be accommodated within a-helical structures albeit with some loss of stability of the structure. PATIC can serve as a useful building block for the synthesis of photoregulated peptides and proteins.

引用

页码：560 / 568

页数：9

共 43 条

[1] CONTROLLING CELL CHEMISTRY WITH CAGED COMPOUNDS
ADAMS, SR
TSIEN, RY
[J]. ANNUAL REVIEW OF PHYSIOLOGY, 1993, 55 : 755 - 784
[2] Peptide oligomers for holographic data storage
Berg, RH
Hvilsted, S
Ramanujam, PS
[J]. NATURE, 1996, 383 (6600) : 505 - 508
[3] SYNTHESIS AND PHOTOCHEMISTRY OF PHOTOLABILE N-GLYCINE DERIVATIVES AND EFFECTS OF ONE ON THE GLYCINE RECEPTOR
BILLINGTON, AP
WALSTROM, KM
RAMESH, D
GUZIKOWSKI, AP
CARPENTER, BK
HESS, GP
[J]. BIOCHEMISTRY, 1992, 31 (24) : 5500 - 5507
[4] A REFINEMENT OF CRYSTAL STRUCTURE OF AZOBENZENE
BROWN, CJ
[J]. ACTA CRYSTALLOGRAPHICA, 1966, 21 : 146 - &
[5] Cammers Goodwin A, 1996, J AM CHEM SOC, V118, P3082, DOI [DOI 10.1021/JA952900Z, 10.1021/ja952900z]
[6] STABILITY OF ALPHA-HELICES
CHAKRABARTTY, A
BALDWIN, RL
[J]. ADVANCES IN PROTEIN CHEMISTRY, VOL 46, 1995, 46 : 141 - 176
[7] A STABLE CIS-AZOBENZENE IN AQUEOUS-SOLUTION
CHAMBERS, EJ
HAWORTH, IS
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (14) : 1631 - 1632
[8] A PHOTOGENERATED PORE-FORMING PROTEIN
CHANG, CY
NIBLACK, B
WALKER, B
BAYLEY, H
[J]. CHEMISTRY & BIOLOGY, 1995, 2 (06): : 391 - 400
[9] Caged catalytic subunit of cAMP-dependent protein kinase
Chang, CY
Fernandez, T
Panchal, R
Bayley, H
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (30) : 7661 - 7662
[10] ELECTRONIC-SPECTRA OF CIS-AZOBENZENES AND TRANS-AZOBENZENES - CONSEQUENCES OF ORTHO SUBSTITUTION
FORBER, CL
KELUSKY, EC
BUNCE, NJ
ZERNER, MC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (21) : 5884 - 5890

← 1 2 3 4 5 →