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47561

Sigma-Aldrich

Fmoc-Trp(Boc)-OH

≥97.0% (HPLC)

Synonym(s):

Nα-Fmoc-N(in)-Boc-L-tryptophan, N(in)-Boc-Nα-Fmoc-L-tryptophan

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About This Item

Empirical Formula (Hill Notation):
C31H30N2O6
CAS Number:
143824-78-6
Molecular Weight:
526.58
Beilstein/REAXYS Number:
7698009
MDL number:
MFCD00153366
UNSPSC Code:
12352209
eCl@ss:
32160406
PubChem Substance ID:
57651011
NACRES:
NA.26

Quality Level

100

assay

≥97.0% (HPLC)

form

solid

optical activity

[α]20/D −21±2°, c = 1% in DMF

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

application(s)

peptide synthesis

functional group

Boc
Fmoc

storage temp.

2-8°C

SMILES string

CC(C)(C)OC(=O)n1cc(C[C@H](NC(=O)OCC2c3ccccc3-c4ccccc24)C(O)=O)c5ccccc15

InChI

1S/C31H30N2O6/c1-31(2,3)39-30(37)33-17-19(20-10-8-9-15-27(20)33)16-26(28(34)35)32-29(36)38-18-25-23-13-6-4-11-21(23)22-12-5-7-14-24(22)25/h4-15,17,25-26H,16,18H2,1-3H3,(H,32,36)(H,34,35)/t26-/m0/s1

InChI key

ADOHASQZJSJZBT-SANMLTNESA-N

Related Categories

Application

Fmoc-Trp(Boc)-OH can be used for the synthesis of analogs of glucagon-like peptide-1 (GLP-1) for the treatment of type 2 diabetes and various peptides by Fmoc solid phase peptide synthesis (SPPS).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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Limiting racemization and aspartimide formation in microwave-enhanced Fmoc solid phase peptide synthesis.
Palasek SA, et al.
Journal of Peptide Science, 13(3), 143-148 (2007)
Potent derivatives of glucagon-like peptide-1 with pharmacokinetic properties suitable for once daily administration.
Knudsen LB, et al.
Journal of Medicinal Chemistry, 43(9), 1664-1669 (2000)
Taru Dube et al.
Amino acids, 49(5), 975-993 (2017-03-12)
Surging reports of peptide-based nanosystems and their growing potency in terms of biological utility demand for the search of newer and simpler peptide-based systems that could serve as smart templates for the development of self-assembled nanostructures. Use of simple amino
Severin J Sigg et al.
Biomacromolecules, 17(3), 935-945 (2016-02-13)
Ever more emerging combined treatments exploiting synergistic effects of drug combinations demand smart, responsive codelivery carriers to reveal their full potential. In this study, a multifunctional stimuli-responsive amphiphilic peptide was designed and synthesized to self-assemble into nanoparticles capable of co-bearing
Solid-phase peptide synthesis: from standard procedures to the synthesis of difficult sequences.
Coin I, et al.
Nature Protocols, 2(12), 3247-3247 (2007)
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