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Merck
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文件

8.52373

Sigma-Aldrich

Fmoc-Cys(STmp)-OH

for peptide synthesis, Novabiochem®

别名:

Fmoc-Cys(STmp)-OH, N-α-Fmoc-S-2,4,6-trimethoxyphenylthio-L-cysteine

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About This Item

经验公式(希尔记法):
C27H27NO7S2
分子量:
541.64
分類程式碼代碼:
12352209
NACRES:
NA.22

product name

Fmoc-Cys(STmp)-OH, Novabiochem®

品質等級

產品線

Novabiochem®

形狀

powder

反應適用性

reaction type: Fmoc solid-phase peptide synthesis

製造商/商標名

Novabiochem®

應用

peptide synthesis

官能基

thiol

儲存溫度

15-25°C

一般說明

Fmoc-Cys(STmp)-OH is a novel new tool for the regioselective synthesis of multiple disulfide bridged peptides by Fmoc SPPS. The STmp group is stable to piperidine but is extremely easy to remove by mild thiolysis. Albericio has reported removing four STmp groups on the solid phase with only three 5 minute treatments of 0.1 M N-methylmorpholine (NMM) in DMF containing 5% DTT.

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS
Fmoc SPPS of Cysteine-Containing Peptides

Literature references:
[1] T. M. Postma, et al. (2012) Org. Lett., 14, 5468.
[2] T. M. Postma & F. Albericio (2013) Org. Lett., 15, 616.

應用

Applications of Fmoc-Cys(STmp)-OH:
  • Synthesis of insulin analogs by regiospecific disulfide bond formation.
  • A review on step-wise introduction of disulfide bonds.
  • Synthesis of human insulin-like peptide 6.

分析報告

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Assay (HPLC, area%): ≥ 94.0 % (a/a)
Purity (TLC(011A)): ≥ 98 %
Solubility (1 mmole in 2 ml DMF): clearly soluble
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.05 %

To see the solvent systems used for TLC of Novabiochem® products please click here.

法律資訊

Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 1

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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N-Chlorosuccinimide, an efficient reagent for on-resin disulfide formation in solid-phase peptide synthesis
T. M. Postma & F. Albericio
Organic Letters, 15, 616-616 (2013)
Chemical Synthesis of Human Insulin-Like Peptide-6
Chemistry?A European Journal , 22, 9777-9777 (2016)
Trimethoxyphenylthio as a highly labile replacement for tert-butylthio cysteine protection in Fmoc solid phase synthesis
T. M. Postma, et al.,
Organic Letters, 14, 5468-5468 (2012)
Synthesis of Four-Disulfide Insulin Analogs via Sequential Disulfide Bond Formation
Fangzhou Wu, et al.
The Journal of Organic Chemistry, 82, 3506-3506 (2017)
Stepwise Construction of Disulfides in Peptides
H Rongjun, et al.,
Chembiochem, 21, 1101-1101 (2020)

商品

Novabiochem® offers orthogonally protected amino acids for peptide synthesis, including cyclic and branched peptides.

Novabiochem® offers orthogonally protected amino acids for peptide synthesis, including cyclic and branched peptides.

Novabiochem® offers orthogonally protected amino acids for peptide synthesis, including cyclic and branched peptides.

Novabiochem® offers orthogonally protected amino acids for peptide synthesis, including cyclic and branched peptides.

实验方案

Overcome challenges in synthesis and disulfide bond formation with protocols for Fmoc solid-phase peptide synthesis of peptides with cysteine and methionine.

Overcome challenges in synthesis and disulfide bond formation with protocols for Fmoc solid-phase peptide synthesis of peptides with cysteine and methionine.

Overcome challenges in synthesis and disulfide bond formation with protocols for Fmoc solid-phase peptide synthesis of peptides with cysteine and methionine.

Overcome challenges in synthesis and disulfide bond formation with protocols for Fmoc solid-phase peptide synthesis of peptides with cysteine and methionine.

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