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Fmoc-Sec(pMeOBzl)-OH

Name: Fmoc-Sec(pMeOBzl)-OH
Brand: MM

≥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

MDL number:

MFCD03788170

UNSPSC Code:

12352209

NACRES:

NA.22

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Properties

Product Name

Fmoc-Sec(pMeOBzl)-OH, Novabiochem^®

Quality Segment

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

SMILES string

[Se](C[C@H](NC(=O)OCC2c3c(cccc3)c4c2cccc4)C(=O)O)Cc1ccc(cc1)OC

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

Description

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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This Item	852069	852028	852187
Sigma-Aldrich 852346 Fmoc-Sec(pMeOBzl)-OH	Sigma-Aldrich 852069 Fmoc-Ser(PO(OBzl)OH)-OH	Sigma-Aldrich 852028 Fmoc-Ser-OH	Sigma-Aldrich 852187 Fmoc-Ser(tBu)-Ser(psiMe,Mepro)-OH
description Novabiochem^®	description Novabiochem^®	description Novabiochem^®	description Novabiochem^®
form powder	form powder	form powder	form powder
functional group Fmoc	functional group Fmoc	functional group hydroxyl	functional group hydroxyl
assay ≥98% (TLC), ≥98.0% (HPLC)	assay ≥90.0% (acidimetric), ≥95.0% (HPLC), ≥97% (TLC)	assay ≥92.0% (acidimetric), ≥98% (TLC), ≥98.0% (HPLC)	assay ≥97% (TLC), ≥97.0% (HPLC)
product line Novabiochem^®	product line Novabiochem^®	product line Novabiochem^®	product line Novabiochem^®
storage temp. 2-8°C	storage temp. −20°C (−15°C to −25°C)	storage temp. 2-30°C	storage temp. 2-8°C
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200

pictograms

GHS06,GHS08,GHS09

signalword

Danger

pcodes

P260 - P273 - P301 + P310 - P302 + P352 - P304 + P340 + P311 - P314

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

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

hcodes

H301 + H331,H315,H335,H373,H410

Storage Class

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

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