Fmoc-D-2-Nal-OH (CAS 138774-94-4), also known as Nα-Fmoc-D-3-(naphthalen-2-yl)alanine, is a Fmoc-protected D-unnatural amino acid of the D-beta-naphthylalanine Fmoc class. This is the Fmoc-SPPS version of the Boc-D-2-Nal-OH building block. It is used to make somatostatin analogues (Lanreotide — D-2-Nal at position 1), GnRH antagonists, and other peptides that need the D-2-Nal residue to be selective for receptors and stable in metabolism. D-2-Nal's big naphthalene side chain interacts with water molecules in receptor binding pockets, which gives it a high affinity and long-lasting effect. In Fmoc-SPPS, HATU/DIPEA or HBTU/DIPEA are used to activate Fmoc-D-2-Nal-OH for coupling. It is very important to control racemization to keep the D-configuration.
ApiSyn sells Fmoc-D-2-Nal-OH (CAS 138774-94-4) as a pharmaceutical-grade specialty D-amino acid building block for Lanreotide and GnRH antagonist SPPS.
| Chemical Name | (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(naphthalen-2-yl)propanoic acid |
| Molecular Formula | C28H23NO4 |
| Molecular Weight | 437.5 |
| CAS Number | 138774-94-4 |