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8.52346

Sigma-Aldrich

Fmoc-Sec(pMeOBzl)-OH

≥98.0% (HPLC), for peptide synthesis, Novabiochem®

Synonym(s):

Fmoc-Sec(pMeOBzl)-OH, Fmoc-Sec(Mob)-OH,Fmoc-S-4-methoxybenzyl selenocysteine

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About This Item

Empirical Formula (Hill Notation):
C26H25NO5Se
CAS Number:
150308-80-8
Molecular Weight:
510.44
UNSPSC Code:
12352209
NACRES:
NA.22

product name

Fmoc-Sec(pMeOBzl)-OH, Novabiochem®

Quality Level

200

product line

Novabiochem®

assay

≥98% (TLC)
≥98.0% (HPLC)

form

powder

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

manufacturer/tradename

Novabiochem®

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

InChI

1S/C26H25NO5Se/c1-31-18-12-10-17(11-13-18)15-33-16-24(25(28)29)27-26(30)32-14-23-21-8-4-2-6-19(21)20-7-3-5-9-22(20)23/h2-13,23-24H,14-16H2,1H3,(H,27,30)(H,28,29)/t24-/m0/s1

InChI key

XCPAYIZRJRMXBI-DEOSSOPVSA-N

Related Categories

General description

Building block for the introduction of selenocysteine during Fmoc SPPS [1,2,3]. Selenocysteine derivatives can undergo enantiomerization during coupling and can form dehydroalanine and β-piperidinylalanine containing side products during subsequent chain elongation [3]. Therefore, activation methods, such as HBTU or PyBOP which involve the addition of a tertiary, base should be avoided for addition of the Sec and all subsequent residues. Cleavage and side-chain deprotection of Sec-containing peptides can be effected using tFA-m-cresol-thioanisole-EDT-water (80:5:5:5:5)[2] or TFA-water-DCM-TIS (89:5:51) at 4 °C [3]. As the Se-pMeOBzl bond is stable to TFA, these methods result in the formation of the corresponding Sev(pMeOBzl) peptide. Peptides containing two Sec(pMeOBzl) residues can be oxidized directly to the corresponding selenocystinyl peptides by treatment with 5-10% DMSO in TFA [1-3].

Associated Protocols and Technical Articles
Cleavage and Deprotection Protocols for Fmoc SPPS

Literature references

[1] T. Koide, et al. (1993) Chem. Pharm. Bull., 41, 502.
[2] T. Koide, et al. (1993) Chem. Pharm. Bull., 41, 1596.
[3] D. Besse & L. Moroder (1997) J. Peptide Sci., 3, 442.

Analysis Note

Color (visual): white to yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Enantiomeric purity: ≥ 99.5 % (a/a)
Purity (TLC(157A)): ≥ 98 %
Assay (HPLC, area%): ≥ 98.0 % (a/a)
Solubility (1 mmole in 2 ml DMF): clearly soluble

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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Danger

Hazard Classifications

Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Skin Irrit. 2 - STOT RE 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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