Solid-phase synthesis of bleomycin group antibiotics. Elaboration of deglycobleomycin A5

Christopher J. Leitheiser; Michael J. Rishel; Xihan Wu; Sidney M. Hecht

doi:10.1021/ol0002469

Solid-phase synthesis of bleomycin group antibiotics. Elaboration of deglycobleomycin A₅

Christopher J. Leitheiser, Michael J. Rishel, Xihan Wu, Sidney M. Hecht

Research output: Contribution to journal › Article › peer-review

24 Scopus citations

Abstract

(matrix presented) The solid-phase syntheses of two deglycobleomycin A₅ analogues were achieved using a commercially available polystyrene resin containing triphenylmethyl-linked spermidine. The final products were deblocked and released from the resin, analyzed, and purified by C₁₈ reversed phase HPLC and characterized by high-field ¹H NMR spectroscopy and mass spectrometry. The purified products relaxed supercoiled plasmid DNA in a concentration-dependent fashion and to the same extent as authentic material derived from natural BLM A₅.

Original language	English (US)
Pages (from-to)	3397-3399
Number of pages	3
Journal	Organic Letters
Volume	2
Issue number	21
DOIs	https://doi.org/10.1021/ol0002469
State	Published - Oct 19 2000
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol0002469

Cite this

@article{d875c518908f4893ae6e1721a99ef035,

title = "Solid-phase synthesis of bleomycin group antibiotics. Elaboration of deglycobleomycin A5",

abstract = "(matrix presented) The solid-phase syntheses of two deglycobleomycin A5 analogues were achieved using a commercially available polystyrene resin containing triphenylmethyl-linked spermidine. The final products were deblocked and released from the resin, analyzed, and purified by C18 reversed phase HPLC and characterized by high-field 1H NMR spectroscopy and mass spectrometry. The purified products relaxed supercoiled plasmid DNA in a concentration-dependent fashion and to the same extent as authentic material derived from natural BLM A5.",

author = "Leitheiser, {Christopher J.} and Rishel, {Michael J.} and Xihan Wu and Hecht, {Sidney M.}",

year = "2000",

month = oct,

day = "19",

doi = "10.1021/ol0002469",

language = "English (US)",

volume = "2",

pages = "3397--3399",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "21",

}

TY - JOUR

T1 - Solid-phase synthesis of bleomycin group antibiotics. Elaboration of deglycobleomycin A5

AU - Leitheiser, Christopher J.

AU - Rishel, Michael J.

AU - Wu, Xihan

AU - Hecht, Sidney M.

PY - 2000/10/19

Y1 - 2000/10/19

N2 - (matrix presented) The solid-phase syntheses of two deglycobleomycin A5 analogues were achieved using a commercially available polystyrene resin containing triphenylmethyl-linked spermidine. The final products were deblocked and released from the resin, analyzed, and purified by C18 reversed phase HPLC and characterized by high-field 1H NMR spectroscopy and mass spectrometry. The purified products relaxed supercoiled plasmid DNA in a concentration-dependent fashion and to the same extent as authentic material derived from natural BLM A5.

AB - (matrix presented) The solid-phase syntheses of two deglycobleomycin A5 analogues were achieved using a commercially available polystyrene resin containing triphenylmethyl-linked spermidine. The final products were deblocked and released from the resin, analyzed, and purified by C18 reversed phase HPLC and characterized by high-field 1H NMR spectroscopy and mass spectrometry. The purified products relaxed supercoiled plasmid DNA in a concentration-dependent fashion and to the same extent as authentic material derived from natural BLM A5.

UR - http://www.scopus.com/inward/record.url?scp=0034687177&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034687177&partnerID=8YFLogxK

U2 - 10.1021/ol0002469

DO - 10.1021/ol0002469

M3 - Article

C2 - 11029220

AN - SCOPUS:0034687177

SN - 1523-7060

VL - 2

SP - 3397

EP - 3399

JO - Organic Letters

JF - Organic Letters

IS - 21

ER -

Solid-phase synthesis of bleomycin group antibiotics. Elaboration of deglycobleomycin A₅

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this