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15500

Sigma-Aldrich

Boc-Ser-OH

≥99.0% (T), for peptide synthesis

Synonym(s):

N-(tert-Butoxycarbonyl)-L-serine, Boc-L-serine

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About This Item

Linear Formula:
HOCH2CH(COOH)NHCOOC(CH3)3
CAS Number:
3262-72-4
Molecular Weight:
205.21
Beilstein:
2212252
EC Number:
221-867-3
MDL number:
MFCD00037243
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57647375
NACRES:
NA.22
Pricing and availability is not currently available.

Product Name

Boc-Ser-OH, ≥99.0% (T)

Assay

≥99.0% (T)

optical activity

[α]20/D −3.5±0.5°, c = 2% in acetic acid

reaction suitability

reaction type: Boc solid-phase peptide synthesis

mp

91 °C (dec.) (lit.)

application(s)

peptide synthesis

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)N[C@@H](CO)C(O)=O

InChI

1S/C8H15NO5/c1-8(2,3)14-7(13)9-5(4-10)6(11)12/h5,10H,4H2,1-3H3,(H,9,13)(H,11,12)/t5-/m0/s1

InChI key

FHOAKXBXYSJBGX-YFKPBYRVSA-N

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General description

Boc-Ser-OH is an amino acid derivative.

Application

Boc-Ser-OH may be used in the synthesis of the following:
  • 2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid (Fmoc: 9-fluorenylmethoxycarbonyl; Boc: t-butyloxycarbonyl)[1]
  • Boc-Ser-Leu-OMe[2]
  • cyclic peptide synthesis[3]
  • benzylsulfonyl-D-Ser-Ser-4-amidinobenzylamide[4]
Building block in peptide synthesis. Starting material for the synthesis of various α-amino acids via the β-lactone.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ9720
BCCB1375
BCBT6324
BCBH7971V
1345058V

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Fmoc-Ser(tBu)-OH ≥98.0% (HPLC)

Sigma-Aldrich

47619

Fmoc-Ser(tBu)-OH

Synthesis of cyclic peptides via O-N-acyl migration.
Lecaillon J, et al.
Tetrahedron Letters, 49(31), 4674-4676 (2008)
M Komai-Koma et al.
Immunology, 91(4), 579-585 (1997-08-01)
The chemoattractant effect of soluble protein antigens for B cells from immunized mice was examined. Mice were immunized either via the footpad with ovalbumin (OVA) in complete Freund's adjuvant (CFA) or with CFA alone; or intraperitoneally with OVA incorporated in
Michael R Carrasco et al.
Biopolymers, 84(4), 414-420 (2006-03-02)
Amino acids with N-alkylaminooxy side chains have proven effective for the rapid synthesis of neoglycopeptides. Chemoselective reaction of reducing sugars with peptides containing these amino acids provides glycoconjugates that are structurally similar to their natural counterparts. 2-(N-Fmoc)-3-(N-Boc-N-methoxy)-diaminopropanoic acid (Fmoc: 9-fluorenylmethoxycarbonyl;
The relationship between taste and primary structure of ?delicious peptide?(Lys-Gly-Asp-Glu-Glu-Ser-Leu-Ala) from beef soup.
Tamura M, et al.
Agricultural and Biological Chemistry, 53(2), 319-325 (1989)
Gema Villa-Fombuena et al.
Development (Cambridge, England), 148(18) (2021-08-10)
Drosophila female germline stem cells (GSCs) are found inside the cellular niche at the tip of the ovary. They undergo asymmetric divisions to renew the stem cell lineage and to produce sibling cystoblasts that will in turn enter differentiation. GSCs
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