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Key Documents

8.52417

Sigma-Aldrich

Fmoc-Cys(Dpm)-OH

Novabiochem®

Synonym(s):

Fmoc-Cys(Dpm)-OH, N-α-Fmoc-S-diphenylmethyl-L-cysteine

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5 G
$68.00
25 G
$272.00

About This Item

Empirical Formula (Hill Notation):
C31H27NO4S
CAS Number:
Molecular Weight:
509.62
MDL number:
UNSPSC Code:
12352209
NACRES:
NA.22

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Quality Level

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(C[C@H](NC(=O)OCC3c4c(cccc4)c5c3cccc5)C(=O)O)C(c2ccccc2)c1ccccc1

InChI

1S/C31H27NO4S/c33-30(34)28(20-37-29(21-11-3-1-4-12-21)22-13-5-2-6-14-22)32-31(35)36-19-27-25-17-9-7-15-23(25)24-16-8-10-18-26(24)27/h1-18,27-29H,19-20H2,(H,32,35)(H,33,34)/t28-/m0/s1

InChI key

IVPLDYIPIHKRET-NDEPHWFRSA-N

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This Item
8.520898.520088.52373
form

powder

form

powder

form

powder

form

powder

functional group

thiol

functional group

amine

functional group

thiol

functional group

thiol

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

product line

Novabiochem®

storage temp.

15-25°C

storage temp.

15-25°C

storage temp.

−20°C (−15°C to −25°C)

storage temp.

15-25°C

Quality Level

200

Quality Level

200

Quality Level

400

Quality Level

200

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

General description

The Dpm group has increased stability compared to Trt, enabling selective removal of Mtt groups on the solid phase with dilute TFA without loss of Dpm groups. Furthermore, the Dpm group is removed by treatment with 95% TFA cleavage cocktails. Racemization during carboxyl activation is lower with this derivative than with Fmoc-Cys(Trt)-OH.

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

Literature references

[1] H. Hibino, et al. (2014) J. Pept. Sci., 20, 30.
[2] M. Góngora-Benítez, et al. (2012) Org.Lett., 14, 5472.

Analysis Note

Colour (visual): white to off white
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (HPLC): ≥ 98.0 % (a/a)
Purity (TLC(011A)): ≥ 98 %
Purity (TLC(0811)): ≥ 98 %
Solubility (1 mmole in 2 ml DMF): clearly soluble
Ethyl acetate (HS-GC): ≤ 0.5 %
Acetate (IC): ≤ 0.1 %

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

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificates of Analysis (COA)

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