Basic information
- CAS
71989-33-8- Standard SMILES
CC(C)(C)OCC(NC(=O)OCC1c2ccccc2-c2ccccc21)C(=O)O- InChIKey
REITVGIIZHFVGU-UHFFFAOYSA-N- Molecular formula
- C22H25NO5
- Average molar mass
- 383.4 g/mol
- Monoisotopic mass
- 383.1732729
Names & identifiers
- Preferred name
- O-(tert-butyl)-N-((9H-fluoren-9-ylmethoxy)carbonyl)-L-serine
- IUPAC
- 2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]propanoic acid
- English name
- FMOC-O-tert-Butyl-L-serine
- Molecular formula
- C22H25NO5
- Molecular weight
- 383.44
Names & synonyms
EINECS 276-260-6O-(tert-Butyl)-N-((9H-fluoren-9-ylmethoxy)carbonyl)-L-serineO-(tert-butyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serineRefChem:366309276-260-671989-33-8N-Fmoc-O-tert-butyl-DL-serine205812-07-33-(tert-butoxy)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)propanoic acidO-tert-Butyl-N-Fmoc-L-serineMFCD00176862Fmoc-D-Ser(But)-OH
Show more names
FMOC-SER(TBU)-OHFMOC-SER(TBU)FMOC-L-SER(TBU)-OHFmoc-Ser(OtBu)-OHFomc-Ser(tBu)-OHFMOC-L-Ser(tBu)-OH 98%FMOC-SER(BUT)Fmoc-Ser(OBut)Fmoc-Ser(tBu)-0HFmoc-L-Ser(OtBu)-OH
N-(9-Fluorenylmethoxycarbonyl)-O-tert-butyl-L-serineSCHEMBL598209FLS-1733-PI3-tert-butoxy-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoic acidAKOS032947705N-alpha-FMOC-O-t-BUTYL-L-SERINELS-14947PD196507
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 84.9 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 8
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 536
Physicochemical properties
- Melting point
- 130.5 · 130.5-135.5 °C(lit.)
- alpha
- 25 · 25 º (c=1,EtOAc 24 ºC)
- Boiling point
- 510.36 °C · 510.36°C (rough estimate)
- Density
- 1.2369 · 1.2369 (rough estimate)
- refractive index
- 24 ° · 24 ° (C=1, AcOEt)
- storage temp.
- 2 · 2-8°C
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- pka
- 3.44 · 3.44±0.10(Predicted)
- form
- powder to crystal
- color
- White to Almost white
- optical activity
- 20 · [α]20/D +25.5±1°, c = 1% in ethyl acetate
- BRN
- 3632013 · 3632013
- Major Application
- peptide synthesis
- InChI
- 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
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 44.4% (4 of 9) of reports.
Warning
H302 (22.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 9 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
REACH registered substance: O-(tert-butyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serine (EC: 276-260-6)
L-Serine, O-(1,1-dimethylethyl)-N-(9H-fluoren-9-ylmethoxy)carbonyl-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (22.2%)
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29242990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24/25-36/37/39-27-26
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesFMOC-O-tert-Butyl-L-serine 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.
General DescriptionL-Serine N-Fmoc (1-13C, 99%) is a protected amino acid used to synthesize isotope-labeled peptides for MS-based protein quantitation.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
北京华美互利生物化工
Related reactions
0 records
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Compound notes
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