2005
DOI: 10.1099/mic.0.27757-0
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Daptomycin biosynthesis in Streptomyces roseosporus: cloning and analysis of the gene cluster and revision of peptide stereochemistry

Abstract: Daptomycin is a 13 amino acid, cyclic lipopeptide produced by a non-ribosomal peptide synthetase (NRPS) mechanism in Streptomyces roseosporus. A 128 kb region of S. roseosporus DNA was cloned and verified by heterologous expression in Streptomyces lividans to contain the daptomycin biosynthetic gene cluster (dpt). The cloned region was completely sequenced and three genes (dptA, dptBC, dptD) encoding the three subunits of an NRPS were identified. The catalytic domains in the subunits, predicted to couple five,… Show more

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Cited by 326 publications
(342 citation statements)
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“…The C-terminal ten amino acids form a macrocyclic core, which contains a ring-closing depsi (ester) bond between the side chain of Thr (4) and the α-COOH of the C-terminal Kyn (13) . 23,24 The N-terminal tripeptide protrudes from the ring and carries the variable fatty acyl residue, which is attached to Trp (1) .…”
Section: Structure and Biosynthesismentioning
confidence: 99%
See 1 more Smart Citation
“…The C-terminal ten amino acids form a macrocyclic core, which contains a ring-closing depsi (ester) bond between the side chain of Thr (4) and the α-COOH of the C-terminal Kyn (13) . 23,24 The N-terminal tripeptide protrudes from the ring and carries the variable fatty acyl residue, which is attached to Trp (1) .…”
Section: Structure and Biosynthesismentioning
confidence: 99%
“…50 At the time of this report, it was not known that daptomycin contains D-Asn rather than L-Asn at position 2; this was discovered only a short time afterwards. 24 Moreover, in all of their analogues, mGlu was replaced with Glu. Consequently, most of their analogues were triple mutants containing Glu in place of mGlu (12) , the unintended L-Asn (2) substitution, as well as an additional substitution of interest at a third position within the peptide.…”
Section: Functional Effects Of Single or Combined Amino Acid Substitumentioning
confidence: 99%
“…12,14 In addition, bioinformatic analysis predicted that A54145 factors would contain D-amino acids at position 2, 8 and 11 (D-Glu 2 , D-Lys 8 and D-Asn 11 ), based on the presence of epimerase domains in the respective NRPS modules. 9 The predicted locations of the D-amino acids coincide with the locations of the three D-amino acids in daptomycin, 16 suggesting that A54145 and daptomycin may have similar three-dimensional structures. The prominent natural variants have either n-decanoic (nC 10 ), iso-decanoic (iC 10 ) or anteiso-undecanoic (aC 11 ) acids attached to the terminal amino group of Trp 1 .…”
Section: Introductionmentioning
confidence: 84%
“…The NRPS mega-enzyme involved in daptomycin biosynthesis in S. roseosporus has three subunits, DptA, DptBC and DptD, 47 which have been exploited in combinatorial biosynthesis. 48 The three subunit arrangement has also been observed in the highly related cryptic daptomycin-like pathway in the finished genome of Saccharopolyspora viridis 49 and the finished biosynthetic gene cluster for taromycin A in the marine Saccharopolyspora sp.…”
Section: Assembly Of Nrps and Pks-i Mega-genes In Draft Genome Sequencesmentioning
confidence: 99%