An efficient synthesis of a probe for protein function: 2,3-diaminopropionic acid with orthogonal protecting groups.
[reaction: see text] An efficient and cost-effective synthesis of N(alpha)-Boc2-N(beta)-Cbz-2,3-diaminopropionic acid is reported. The synthesis starts from commercially available N(alpha)-Boc-Asp(OBn)-OH and employs a Curtius rearrangement to establish the beta-nitrogen. Proper protection of the alpha-nitrogen is essential for the success of the Curtius rearrangement.
Englund
Ethan A
EA
Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA.
Gopi
Hosahudya N
HN
Appella
Daniel H
DH
D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D011506:Proteins / Q000737:chemistry / Q000502:physiology*; D015091:beta-Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
D011506:Proteins; D015091:beta-Alanine; C011757:2,3-diaminopropionic acid; D009584:Nitrogen