Synthesis of linear gramicidin requires the cooperation of two independent reductases

被引:23
作者
Schracke, N [1 ]
Linne, U [1 ]
Mahlert, C [1 ]
Marahiel, MA [1 ]
机构
[1] Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany
关键词
D O I
10.1021/bi050074t
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The linear pentadecapeptide gramicidin has been reported to be assembled by four large multimodular nonribosomal peptide synthetases (NRPSs), LgrABCD, that comprise 16 modules. During biosynthesis, the N-formylated 16mer peptide is bound to the peptidyl carrier protein (PCP) of the terminal module via a thioester bond to the carboxyl group of the last amino acid glycine(16). In a first reaction the peptide is released from the protein template in an NAD(P)H-dependent reduction step catalyzed by the adjacent reductase forming an aldehyde intermediate. Here we present the biochemical proof that this aldehyde intermediate is further reduced by an aldoreductase, LgrE, in an NADPH-dependent manner to form the final product gramicidin A, N-formyl-pentadecapeptide-ethanolamine. To determine the potential use of the two reductases in the construction of hybrid NRPSs, we have tested their ability to accept a variety of different substrates in vitro. The results obtained give way to a broad spectrum of possible use.
引用
收藏
页码:8507 / 8513
页数:7
相关论文
共 33 条
  • [21] A NEW MYXOCOCCUS-XANTHUS GENE-CLUSTER FOR THE BIOSYNTHESIS OF THE ANTIBIOTIC SAFRAMYCIN MX1 ENCODING A PEPTIDE SYNTHETASE
    POSPIECH, A
    CLUZEL, B
    BIETENHADER, J
    SCHUPP, T
    [J]. MICROBIOLOGY-SGM, 1995, 141 : 1793 - 1803
  • [22] GRAMICIDIN A .V. STRUCTURE OF VALINE-AND ISOLEUCINE-GRAMICIDIN A
    SARGES, R
    WITKOP, B
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (09) : 2011 - +
  • [23] Nonribosomal peptides: from genes to products
    Schwarzer, D
    Finking, R
    Marahiel, MA
    [J]. NATURAL PRODUCT REPORTS, 2003, 20 (03) : 275 - 287
  • [24] Learning from nature's drug factories: Nonribosomal synthesis of macrocyclic peptides
    Sieber, SA
    Marahiel, MA
    [J]. JOURNAL OF BACTERIOLOGY, 2003, 185 (24) : 7036 - 7043
  • [25] Loading peptidyl-coenzyme A onto peptidyl carrier proteins: A novel approach in characterizing macrocyclization by thioesterase domains
    Sieber, SA
    Walsh, CT
    Marahiel, MA
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10862 - 10866
  • [26] New lessons of combinatorial biosynthesis from myxobacteria -: The myxothiazol biosynthetic gene cluster of Stigmatella aurantiaca DW4/3-1
    Silakowski, B
    Schairer, HU
    Ehret, H
    Kunze, B
    Weinig, S
    Nordsiek, G
    Brandt, P
    Blöcker, H
    Höfle, G
    Beyer, S
    Müller, R
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1999, 274 (52) : 37391 - 37399
  • [27] MODULAR STRUCTURE OF PEPTIDE SYNTHETASES REVEALED BY DISSECTION OF THE MULTIFUNCTIONAL ENZYME GRSA
    STACHELHAUS, T
    MARAHIEL, MA
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1995, 270 (11) : 6163 - 6169
  • [28] Biochemical characterization of peptides carrier protein (PCP), the thiolation domain of multifunctional peptide synthetases
    Stachelhaus, T
    Huser, A
    Marahiel, MA
    [J]. CHEMISTRY & BIOLOGY, 1996, 3 (11): : 913 - 921
  • [29] Peptide bond formation in nonribosomal peptide biosynthesis - Catalytic role of the condensation domain
    Stachelhaus, T
    Mootz, HD
    Bergendahl, V
    Marahiel, MA
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 1998, 273 (35) : 22773 - 22781
  • [30] The specificity-conferring code of adenylation domains in nonribosomal peptide synthetases
    Stachelhaus, T
    Mootz, HD
    Marahiel, MA
    [J]. CHEMISTRY & BIOLOGY, 1999, 6 (08): : 493 - 505