17249
α-Methyl-L-proline
≥98.0% (TLC)
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About This Item
Empirical Formula (Hill Notation):
C6H11NO2
CAS Number:
Molecular Weight:
129.16
UNSPSC Code:
12352209
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
4350211
Quality Level
assay
≥98.0% (TLC)
reaction suitability
reaction type: solution phase peptide synthesis
application(s)
peptide synthesis
SMILES string
C[C@]1(CCCN1)C(O)=O
InChI
1S/C6H11NO2/c1-6(5(8)9)3-2-4-7-6/h7H,2-4H2,1H3,(H,8,9)/t6-/m0/s1
InChI key
LWHHAVWYGIBIEU-LURJTMIESA-N
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Articles
Proline analogues are promising candidates for tuning the biological, pharmaceutical, or physicochemical properties of naturally occuring, as well as de novo designed, linear, and, cyclic peptides.
S Thaisrivongs et al.
Journal of medicinal chemistry, 30(3), 536-541 (1987-03-01)
A structure-activity analysis of peptides containing backbone C alpha-methyl modification at the P4 site of the angiotensinogen sequence led to the discovery of potent renin inhibitors with apparent in vitro metabolic stability. Boc-alpha-MePro-Phe-His-Leu psi[CHOHCH2]Val-Ile-Amp dicitrate (Va) is a potent inhibitor
Alessandro Moretto et al.
Biopolymers, 89(5), 465-470 (2007-09-07)
Methylation at the C(alpha)-position of a Pro residue was expected to lock the preceding tertiary amide (omega) torsion angle of the resulting (alphaMe)Pro to the trans disposition and to restrict the phi,psi surface to the single region where the 3(10)/alpha-helices
J H Welsh et al.
FEBS letters, 297(3), 216-220 (1992-02-10)
The ability of (S)-alpha-methylproline (alpha-MePro) to stabilise reverse-turn conformations in the peptide hormone bradykinin (BK = Arg1-Pro2-Pro3-Gly4-Phe5-Ser6-Pro7-Phe8-Arg9) has been investigated. Two BK analogues containing alpha-MePro at position 3 or position 7 were synthesised and their conformations in aqueous solution investigated
Global Trade Item Number
| SKU | GTIN |
|---|---|
| PHR8965-50MG | 04065266399547 |
| 17249-250MG | 04061832593999 |
| 17249-1G | 04061834411314 |