8.52373
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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关于此项目
经验公式（希尔记法）:
C27H27NO7S2
化学文摘社编号:
分子量:
541.64
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22
产品名称
Fmoc-Cys(STmp)-OH, Novabiochem®
Quality Segment
product line
Novabiochem®
form
powder
reaction suitability
reaction type: Fmoc solid-phase peptide synthesis
manufacturer/tradename
Novabiochem®
application(s)
peptide synthesis
functional group
thiol
storage temp.
15-25°C
SMILES string
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
General description
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.
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.
Application
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.
Analysis Note
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.
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.
Legal Information
Novabiochem is a registered trademark of Merck KGaA, Darmstadt, Germany
存储类别
11 - Combustible Solids
wgk
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable