Combinatorial chemistry of natural products: Solid phase synthesis of D- and L-cycloserine derivatives

Gordeev, M. F.; Luehr, Gary W.; Hui, Hon; Gordon, Eric M.; Patel, Dinesh V.

doi:10.1016/s0040-4020(98)00997-1

Cited by 41 publications

(23 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The Fmocloading of the resin was determined by standard procedures used to calculate the hydroxyl loading. [12] Polystyrene-bound aldehyde (21): IBX (2.99 g, 11.07 mmol) was added to a suspension of polystyrene-bound alcohol 20 (4.5 g, 3.69 mmol) in THF/ DMSO (1:1, 90 mL). The mixture was shaken for 18 h at room temperature and then filtered.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Development of the Traceless Phenylhydrazide Linker for Solid‐Phase Synthesis

Stieber¹,

Grether²,

Waldmann³

2003

Chemistry A European J

View full text Add to dashboard Cite

The hydrazide group is a new oxidatively cleavable traceless linker for solid-phase chemistry. It can be readily introduced by hydrazide formation between a carboxy-functionalized resin and different substituted hydrazines. In order to achieve high yields in this step, new carboxylic acid resins were developed that are not prone to undesired imide formation upon activation of the carboxylic acid. The polymer-bound acyl hydrazides were successfully employed in various transformations, namely Heck, Suzuki, Sonogashira, and Stille couplings, as well as Wittig and Grignard reactions. Traceless release of the coupling products from the solid support is achieved selectively under mild conditions and in high purity by oxidation of the aryl hydrazides to acyl diazenes with Cu(II) salts or N-bromosuccinimide (NBS) and subsequent nucleophilic attack of the acyl diazene intermediates. Traceless cleavage by oxidation with NBS can be carried out as a two-step process in which stable acyl diazenes are first generated by treatment with NBS in the absence of a nucleophile. After removal of the reagents by simple resin washing, the traceless release is effected by the addition of methanol, which leads to products of high purity without any additional separation steps.

show abstract

Section: Methodsmentioning

confidence: 99%

“…The loading of polymeric support 20 was determined by acylation with Fmoc-Cl, cleavage of the carbonate, and UV-spectrometric determination of the released fulvene. [12] The loading of resin 22 was determined as described above for polymeric support 17.…”

mentioning

confidence: 99%

Development of the Traceless Phenylhydrazide Linker for Solid‐Phase Synthesis

Stieber¹,

Grether²,

Waldmann³

2003

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…D-enantiomer cycloserine is the most abundant and thus the cheapest ($30/g). Hydrolysis of cycloserine under acidic conditions is known to produce Ams [27,45,46], Exploiting this chemistry, we succeeded in making Fmoc-D-Ams(Boc)-OH from cycloserine in three steps (Scheme 4): nucleophilicity, analogous to acylated hydroxylamines as discussed above [47], and in some batches the N,N%-bis-Fmoc compound was formed as a byproduct [56]. Recrystallization from iso-propanol yielded pure Fmoc-cycloserine 6.…”

Section: Synthesis Of Building Blocks Fmoc-d-ams(boc)-oh 1 and Fmocmentioning

confidence: 99%

“…H-NMR (CDCl 3 ) l: 7.76 (d, 2H, 7.6 Hz, ArH), 7.61 (d, 2H, 7.3 Hz, ArH), 7.40 (t, 2H, 7.5 Hz, ArH), 7.312 An alternative route to Fmoc-cycloserine was reported very recently. The synthesis was performed via bis-silyated cycloserine[56].Copyright © 1999 European Peptide Society and John Wiley & Sons, Ltd. J. Peptide Sci. 5: 582 -592 (1999)…”

mentioning

confidence: 99%

Preparation and application ofO-amino-serine, Ams, a new building block in chemoselective ligation chemistry

Spetzler

Høeg-Jensen

1999

J. Peptide Sci.

View full text Add to dashboard Cite

The non-codable amino acid O-amino-serine, Ams, has been prepared in both L- and D-forms as the orthogonally protected derivative, Fmoc-Ams(Boc)-OH (1 and 2). This new amino acid derivative is useful for chemoselective ligations. Under acidic conditions and in the presence of all other common amino acid functionalities, the oxyamine function selectively forms oxime linkages with aldehydes. The Ams residue has been incorporated into both ends of the peptide sequence Asp-Leu-Trp-Gln-Lys using standard SPPS. The deprotected peptide has been used for chemical ligation to afford a peptide dimer as well as a glycopeptide. Ams racemization was found to be negligible, as monitored by HPLC separation of Ams dipeptide diastereomers.

show abstract

“…Knoevenagel condensations (KC) [16] [17] which are one of the most important CÀC bond forming reactions have been widely used in the synthesis of important intermediates or products for perfumes [25], pharmaceuticals [26], calcium antagonists [27], and polymers [28]. Thus, the development of new synthetic procedures for KC has attracted the attention of organic chemists.…”

mentioning

confidence: 99%