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Merck
CN

47619

Fmoc-Ser(tBu)-OH

≥98.0% (HPLC), for peptide synthesis

Synonym(s):

Fmoc-O-tert-butyl-L-serine

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About This Item

Empirical Formula (Hill Notation):
C22H25NO5
CAS Number:
Molecular Weight:
383.44
NACRES:
NA.26
PubChem Substance ID:
eCl@ss:
32160406
UNSPSC Code:
12352209
EC Number:
276-260-6
MDL number:
Beilstein/REAXYS Number:
3632013
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Product Name

Fmoc-Ser(tBu)-OH, ≥98.0% (HPLC)

Quality Level

assay

≥98.0% (HPLC)

form

powder

optical activity

[α]20/D +25.5±1°, c = 1% in ethyl acetate

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Fmoc

storage temp.

2-8°C

SMILES string

CC(C)(C)OC[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(O)=O

InChI

1S/C22H25NO5/c1-22(2,3)28-13-19(20(24)25)23-21(26)27-12-18-16-10-6-4-8-14(16)15-9-5-7-11-17(15)18/h4-11,18-19H,12-13H2,1-3H3,(H,23,26)(H,24,25)/t19-/m0/s1

InChI key

REITVGIIZHFVGU-IBGZPJMESA-N

Application

Fmoc-Ser(tBu)-OH is an N-terminal protected reagent used in the peptide synthesis. Some of the reported examples are:
  • Total synthesis of an antibiotic, daptomycin, by cyclization via a chemoselective serine ligation.
  • Preparation of MUC1, a T-cell helper peptide, using iterative pentafluorophenyl ester-mediated fragment condensations.
  • Linear solid-phase peptide synthesis of ubiquitin and diubiquitin.



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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)



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Total synthesis of daptomycin by cyclization via a chemoselective serine ligation.
Lam H Y, et al.
Journal of the American Chemical Society, 135(16), 6272-6279 (2013)
Advances in proline ligation.
Townsend S D, et al.
Journal of the American Chemical Society, 134(8), 3912-3916 (2012)
Chemical synthesis of ubiquitin, ubiquitin?based probes, and diubiquitin.
El Oualid F, et al.
Angewandte Chemie (International Edition in English), 49(52), 10149-10153 (2010)



Global Trade Item Number

SKUGTIN
367796-250MG04061833482421
47619-25G-F04061832362151
47619-100G-F04061832362137
47619-10G-F04061832362144
47619-1KG-F04061826222652