International Journal of Peptide Research and Therapeutics
Koketsu M, Nada F, Hiramatsu S, Ishihara H (2002) Reactions of acyl
chlorides with LiAlHSeH. Preparation of diacylselenides, dia-
cyldiselenides, selenocarboxylates and cyclic selenoanhydrides.
J Chem Soc Perkin Trans 1:737–740
Compliance with Ethical Standards
Conflict of interest The authors declare that this article content has no
conflicts of interest.
Krishnamurty M, Vishwanatha TM, Nageswararao P, Panduranga V,
Sureshbabu VV (2015) Iodine-mediated oxidative coupling of
hydroxamic acids with amines towards a new peptide-bond for-
mation. Synlett 26:2565–2569
Ethical Approval This article does not contain any studies with human
participants or animals performed by any of the authors.
Lara RM, Nicholas JM, Payne RJ (2014) Peptide ligation chemistry at
selenol amino acids. J Pept Sci 20:64–77
Informed Consent The article does not contain any studies in patients
by any of the authors.
Madhu C, Vishwanatha TM, Sureshbabu VV (2013) An efficient syn-
α
thesis of N -protected amino and peptide acid aryl amides via
α
iodine-mediated oxidative acylation of N -protected amino and
peptide thioacids. Synthesis 45:2727–2736
References
Mali SM, Gopi HN (2014) Thioacetic acid/NaSH-mediated synthesis
of N-protected amino thioacids and their utility in peptide synthe-
sis. J Org Chem 79:2377–2383
Ananda K, Sureshbabu VV (2000) Synthesis of peptides employing
Fmoc-/Boc-/Z-amino acid fluorides and activated commercial
zinc dust. Lett Pept Sci 7:41–46
Malins LR, Payne R (2012) Synthesis and utility of β-selenol-
phenylalanine for native chemical ligation-deselenization chem-
istry. J Org Lett 14:3142–3145
Andrea T, Francesca P, Lucio M, Massimo C, Carlo S (2017) General,
mild, and metal-free synthesis of phenyl selenoesters from anhy-
drides and their use in peptide synthesis. J Org Chem 82:4588–4603
Dawson PE, Muir TW, Lewis CL, Kent SB (1994) Synthesis of protein
by native chemical ligation. Science 266:776–779
Malins LR, Payne RJ (2014) Recent extensions to native chemical liga-
tion for the chemical synthesis of peptides and proteins. Curr Opin
Chem Biol 22:70–78
McGrath NA, Raines RT (2011) Chemoselectivity in chemical biol-
ogy: acyltransfer reactions with sulfur and selenium. Acc Chem
Res 44:752–761
Durek T, Alewood PF (2011) Preformed selenoesters enable rapid
native chemical ligation atintractable sites. Angew Chem Int Ed
5
0:12042–12045
Mitchell NJ, Malins LR, Liu X, Thompson RE, Chan B, Radom L,
Payne RJ (2015) Rapid additive-free selenocystine—selenoester
peptide ligation. J Am Chem Soc 137:14011–14014
Nageswararao P, Panduranga V, Prabhu G, Vishwanatha TM, Suresh-
Fischbach MA, Walsh CT (2006) Assembly-Line enzymology for pol-
yketide and nonribosomal peptide antibiotics: logic, machinery,
and mechanisms. Chem Rev 106:3468–3496
β
Funabashi M, Yang Z, Nonaka K, Hosobuchi M, Fujita Y, Shibata T,
Chi X, Vanlenen SG (2010) An ATP independent strategy for
amide bond formation in antibiotic biosynthesis. Nat Chem Biol
l6:581–586
babu VV (2015) Synthesis of chiral N -protected amino dis-
elenides from the corresponding amino alkyl iodides using
NaBH Se as a selenating reagent and their conversion to seleninic
2
3
acids. RSC Adv 5:51807–51811
Gasparo MD, Whitebread S (1995) Binding of valsartan to mammalian
Nishiyama Y, Katsuura A, Okamoto Y, Hamanaka S (1989) Bis (acyl)
diselenides as convenient acyling reagents. Chem Lett 1825–1826
Niyomura O, Tani K, Kato S (1999) A facile synthesis of potassium
angiotensin AT receptors. RegulPept 59:303–311
1
Gieselman MD, Xie L, Van der Donk WA (2001) Synthesis of a sele-
nocysteine-containing peptide by native chemical ligation. Org
Lett 3:1331–1334
selenocarboxylates and their oxidation with XeF to diacyldis-
2
elenides: an X-ray structural analysis of di(4-methoxybenzoyl)
Gowd KH, Blais KD, Elmslie KS, Steiner AM, Olivera BM, Bulaj G
diselenide. Heteroat Chem 10:373–379
(2012) Dissecting a role of evolutionary—conserved but noncriti-
Patchett AA (1993) Excursions in drug discovery. J Med Chem
36:2051–2058
cal disulphide bridges in cysteine-rich peptides using ω-conotoxin
GVIA and its selenocysteineanalogs. Biopolymers 98:212–223
Greenberg A, Breneman CM, Liebman JF (2000) The amide link-
age: selected structural aspects in chemistry, biochemistry and
materials science. Wiley-Interscience, New York
Pattabiraman VR, Bode JW (2011) Rethinking amide bond synthesis.
Nature 480:471
Prabhu G, Narendra N, Panduranga V, Sureshbabu VV (2015) Amino
acid fluorides: viable tools for synthesis of peptides, peptidomi-
metics and enantiopureheterocycles. RSC Adv 5:48331
Rasale DB, Maity I, Das AK (2014) In situ generation of redox active
peptides driven by selenoester mediated native chemical ligation.
Chem Commun 50:11397–11400
Hemantha HP, Narendra N, Sureshbabu VV (2012) Total chemical
synthesis of polypeptides and proteins: chemistry of ligation
techniques and beyond. Tetrahedron 68:9491–9537
Hondal RJ (2005) Incorporation of selenocysteine into proteins using
peptide ligation. Protein Pept Lett 12:757–764
Sewald N, Jakubke HD (2002) Peptide synthesis peptides: chemistry
and biology, Wiley, Weinheim, pp 135–267
Hondal RJ, Marino SM, Gladyshev VN (2013) Selenocysteine in
thiol/disulfide-like exchange reactions. Antioxid Redox Signal
Simonovic M, Steitz TA (2009) A structural view on the mechanism of
the ribosome-catalyzed peptide bond formation. Biochem Biophys
Acta 1789:612–623
1
8:1675–1689
Huber RE, Criddle RS (1967) Comparison of the chemical proper-
ties of selenocysteine and selenocystine with their sulfurana-
logs. Arch Bio chem Biophys 122:164–173
Steinmann D, Nauser T, Koppenol WH (2010) Selenium and sul-
fur in exchange reactions: a comparative study. J Org Chem
75:6696–6699
Ishihara H, Kato S (1972) Selenol and selenonesters containing organ
group IV metals. Tetrahedron Lett 3751–3754
Tantry SJ, Vasanthakumar GR, Sureshbabu VV (2003) Synthesis of
peptides employing 9-fluorenylmethyl chloroformate as a coupling
agent. Lett Pept Sci 10:51–55
Ishihara H, Sato S, Hirabayashi Y (1977) The synthesis and properties
of diacyl selenides. Bull Chem Soc Jpn 50:3007–3009
Jensen KA, Bøje L, Henriksen L (1972) Organic selenium compounds
XVIII on the existence of monoselenocarboxylic acids. Acta
Chem Scand 26:1465–1470
Thapa P, Zhang RY, Menon V, Bingham JP (2014) Native chemical
ligation: a boon to peptide chemistry. Molecules 19:14461–14483
Vázquez O, Seitz O (2014) Templated native chemical ligation: peptide
chemistry beyond protein synthesis. J Pept Sci 20:78–86
Kent SBH (2009) Total chemical synthesis of proteins. Chem Soc Rev
3
8:338–351
1
3