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8.52373

Sigma-Aldrich

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 EA
CN¥5,896.35

CN¥5,896.35

Available to ship onApril 14, 2025Details

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About This Item

Empirical Formula (Hill Notation):
C27H27NO7S2
CAS Number:
1403834-74-1
Molecular Weight:
541.64
MDL number:
MFCD27957369
UNSPSC Code:
12352209
NACRES:
NA.22

CN¥5,896.35

Available to ship onApril 14, 2025Details

Sign In for Best Price
Request a Bulk Order

Product Name

Fmoc-Cys(STmp)-OH, Novabiochem®

Quality Level

200

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

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SUPELCOSIL™ LC-18 HPLC Column 5 μm particle size, L × I.D. 25 cm × 4.6 mm

58298

SUPELCOSIL™ LC-18 HPLC Column

SUPELCOSIL™ LC-18 HPLC Column 5 μm particle size, L × I.D. 25 cm × 21.2 mm

54849

SUPELCOSIL™ LC-18 HPLC Column

SUPELCOSIL™ LC-18 HPLC Column 5 μm particle size, L × I.D. 15 cm × 2.1 mm

57934

SUPELCOSIL™ LC-18 HPLC Column

SUPELCOSIL™ LC-18 HPLC Column 5 μm particle size, L × I.D. 25 cm × 2.1 mm

57935

SUPELCOSIL™ LC-18 HPLC Column

separation technique

reversed phase

separation technique

reversed phase

separation technique

reversed phase

separation technique

reversed phase

matrix

silica gel, spherical particle platform

matrix

silica gel, spherical particle platform

matrix

silica gel, spherical particle platform

matrix

silica gel, spherical particle platform

particle size

5 μm

particle size

5 μm

particle size

5 μm

particle size

5 μm

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

technique(s)

HPLC: suitable

agency

suitable for USP L1

agency

suitable for USP L1

agency

suitable for USP L1

agency

suitable for USP L1

General description

Fmoc-Cys(STmp)-OH is a novel new tool for the regioselective synthesis of multiple disulfide bridged peptides by Fmoc SPPS.[1] 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.[2]

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.[3]
  • A review on step-wise introduction of disulfide bonds.[4]
  • Synthesis of human insulin-like peptide 6.[5]

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

新产品

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    Find documentation for the products that you have recently purchased in the Document Library.

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    Synthesis of Four-Disulfide Insulin Analogs via Sequential Disulfide Bond Formation
    Fangzhou Wu, et al.
    The Journal of Organic Chemistry, 82, 3506-3506 (2017)
    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)
    Chemical Synthesis of Human Insulin-Like Peptide-6
    Chemistry?A European Journal , 22, 9777-9777 (2016)
    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)
    Stepwise Construction of Disulfides in Peptides
    H Rongjun, et al.,
    Chembiochem, 21, 1101-1101 (2020)

    Articles

    Selecting Orthogonal Building Blocks

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

    Protocols

    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.

    Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

    Contact Technical Service