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8.52373

Fmoc-Cys(STmp)-OH

for peptide synthesis, Novabiochem®

Synonym(s):

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

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1 g
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$409.00
$306.75
5 g
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$1,990.00

About This Item

Empirical Formula (Hill Notation):
C27H27NO7S2
CAS Number:
Molecular Weight:
541.64
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22

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Product Name

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.

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.

Legal Information

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

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This Item
852008852094852031
description

Novabiochem®

description

Novabiochem®

description

Novabiochem®

description

Novabiochem®

form

powder

form

powder

form

powder

form

powder

functional group

thiol

functional group

thiol

functional group

amine

functional group

thiol

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

storage temp.

15-25°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

15-25°C

Quality Level

200

Quality Level

400

Quality Level

200

Quality Level

200

application(s)

peptide synthesis

application(s)

peptide synthesis

application(s)

peptide synthesis

application(s)

peptide synthesis


Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable



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