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安全信息

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
CAS号:
1403834-74-1
分子量:
541.64
MDL编号:
MFCD27957369
UNSPSC代码:
12352209
NACRES:
NA.22

产品名称

Fmoc-Cys(STmp)-OH, Novabiochem®

质量水平

200

产品线

Novabiochem®

表单

powder

反应适用性

reaction type: Fmoc solid-phase peptide synthesis

制造商/商品名称

Novabiochem®

应用

peptide synthesis

官能团

thiol

储存温度

15-25°C

SMILES字符串

S(Sc4c(cc(cc4OC)OC)OC)C[C@H](NC(=O)OCC1c2c(cccc2)c3c1cccc3)C(=O)O

InChI

1S/C27H27NO7S2/c1-32-16-12-23(33-2)25(24(13-16)34-3)37-36-15-22(26(29)30)28-27(31)35-14-21-19-10-6-4-8-17(19)18-9-5-7-11-20(18)21/h4-13,21-22H,14-15H2,1-3H3,(H,28,31)(H,29,30)/t22-/m0/s1

InChI key

GADCBXMSWHDNAU-QFIPXVFZSA-N

相关类别

一般描述

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.

应用

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.

分析说明

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.

法律信息

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

储存分类代码

11 - Combustible Solids

WGK

WGK 1

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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Stepwise Construction of Disulfides in Peptides
H Rongjun, et al.,
Chembiochem, 21, 1101-1101 (2020)
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)
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)

商品

Selecting Orthogonal Building Blocks

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

实验方案

Protocols for the Fmoc SPPS of Cysteine-Containing Peptides

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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